Sulfonamide derivatives, insecticides for agricultural and horticultural use, and usage thereof

ABSTRACT

Sulfonamide derivatives represented by general formula (I) or salts thereof; insecticides for agricultural and horticultural use containing the same as the active ingredient; and usage thereof: 
                         
[wherein A is optionally substituted (C 1 –C 6 )alkylene, (C 3 –C 6 )alkenylene or the like; R 1  is H, optionally substituted (C 1 –C 6 )alkyl, (C 3 –C 6 )alkenyl, (C 3 –C 6 )cycloalkyl or the like; R 2 , R 3  and R 4  are each H, (C 1 –C 6 )alkyl, (C 3 –C 6 )alkenyl or the like, or R 2  and A or R 2  and R 1  may form a 3- to 8-membered ring which may be interrupted by one to three atoms selected from among O, S and N; Q is C or N; X and Y are each halogen, CN, NO 2 , (C 1 –C 6 )alkyl, (C 2 –C 6 )alkenyl or the like; m is 0 to 2; n is 0 to 3; and two adjacent Xs or Ys on the aromatic ring may be united to form a fused ring]. The compounds exhibit excellent insecticidal activity against insect pests resistant to existing pesticides even when applied in dosages lower than those of similar pesticides.

This application is the national phase of international applicationPCT/JP03/10774 filed 26 Aug. 2003 which designated the U.S.

TECHNICAL FIELD

The present invention relates to sulfonamide derivatives or saltsthereof, agricultural and horticultural insecticides containing any ofsaid compounds as an active ingredient, and their usage.

BACKGROUND ART

Compounds analogous to the sulfonamide derivatives of the presentinvention have been known to be useful as agricultural and horticulturalinsecticides (see, for example, JP-A-11-240857 or JP-A-2001-131141).These references, however, do not describe working examples, physicalproperties and the like with respect to the compounds represented bygeneral formula (I) of the present invention.

The production of agricultural and horticultural crops and the like isstill badly damaged by insect pests and the like, and the development ofa novel agricultural and horticultural insecticide is desired becauseof, for example, the appearance of insect pests resistant to existingchemicals. In addition, because of the increased population of agedfarmers, and the like, various labor-saving application methods aredesired and the development of an agricultural and horticulturalinsecticide having properties suitable for the application methods isdesired.

DISCLOSURE OF THE INVENTION

The present inventors earnestly investigated in order to develop a novelagricultural and horticultural insecticide, and consequently found thatthe sulfonamide derivatives represented by general formula (I) or saltsthereof of the present invention are novel compounds not known in anyliterature and are excellent agricultural and horticultural insecticideswhich are effective at a lower dosage as compared with the analogouscompounds disclosed in the above prior art references, whereby thepresent invention has been accomplished.

That is, the present invention relates to sulfonamide derivativesrepresented by general formula (I), or salts thereof:

wherein A is a (C₁–C₆)alkylene group; a substituted (C₁–C₆)alkylenegroup having one or more substituents which may be the same or differentand are selected from halogen atoms, cyano group, nitro group,(C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups,halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups,halo(C₁–C₆)alkylsulfonyl groups, mono(C₁–C₆)alkylamino groups anddi(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent; a (C₃–C₆)alkenylene group; a substituted (C₃–C₆)alkenylenegroup having one or more substituents which may be the same or differentand are selected from halogen atoms, cyano group, nitro group,(C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups,halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups,halo(C₁–C₆)alkylsulfonyl groups, mono(C₁–C₆)alkylamino groups anddi(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent; a (C₃–C₆)alkynylene group; or a substituted (C₃–C₆)alkynylenegroup having one or more substituents which may be the same or differentand are selected from halogen atoms, cyano group, nitro group,(C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups,halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups,halo(C₁–C₆)alkylsulfonyl groups, mono(C₁–C₆)alkylamino groups anddi(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent; any saturated carbon atom in the (C₁–C₆)alkylene group,substituted (C₁–C₆)alkylene group, (C₃–C₆)alkenylene group, substituted(C₃–C₆)alkenylene group, (C₃–C₆)alkynylene group or substituted(C₃–C₆)alkynylene group may be substituted by a (C₂–C₅)alkylene group soas to form a (C₃–C₆)cycloalkane ring, and any two carbon atoms in the(C₂–C₆)alkylene group, substituted (C₂–C₆)alkylene group,(C₃–C₆)alkenylene group or substituted (C₃–C₆)alkenylene group may betaken together with an alkylene group or an alkenylene group so as torepresent a (C₃–C₆)cycloalkane ring or a (C₃–C₆)cycloalkene ring;

R¹ is a hydrogen atom; a (C₁–C₆)alkyl group; a substituted (C₁–C₆)alkylgroup having one or more substituents which may be the same or differentand are selected from halogen atoms, cyano group, nitro group, hydroxylgroup, (C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthiogroups, halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups,halo(C₁–C₆)alkylsulfonyl groups, mono(C₁–C₆)alkylamino groups,mono(halo(C₁–C₆)alkyl)amino groups, di(C₁–C₆)alkylamino groups whose(C₁–C₆)alkyl groups may be the same or different,di(halo(C₁–C₆)alkyl)amino groups whose halo(C₁–C₆)alkyl groups may bethe same or different, (C₁–C₆)alkoxycarbonyl groups,(C₁–C₆)alkylaminocarbonyl groups, (C₁–C₆)alkylcarbonyloxy groups,phenoxy group, substituted phenoxy groups having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups,(C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups,halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups,halo(C₁–C₆)alkylsulfonyl groups and (C₁–C₆)alkoxycarbonyl groups,phenylthio group, substituted phenylthio groups having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁–C₆)alkyl groups, halo (C₁–C₆)alkyl groups,(C₁–C₆)alkoxy groups, halo (C₁–C₆)alkoxy groups, (C₁–C₆)alkylthiogroups, halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups,halo(C₁–C₆)alkylsulfonyl groups and (C₁–C₆)alkoxycarbonyl groups, phenylgroup, substituted phenyl groups having one or more substituents whichmay be the same or different and are selected from halogen atoms, cyanogroup, nitro group, (C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups,(C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxy groups, mono(C₁–C₆)alkylaminogroups, di(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be thesame or different, (C₁–C₆)alkylthio groups, halo(C₁–C₆)alkylthio groups,(C₁–C₆)alkylsulfinyl groups, halo(C₁–C₆)alkylsulfinyl groups,(C₁–C₆)alkylsulfonyl groups, halo(C₁–C₆)alkylsulfonyl groups and(C₁–C₆)alkoxycarbonyl groups, pyridyl group, and substituted pyridylgroups having one or more substituents which may be the same ordifferent and are selected from halogen atoms, cyano group, nitro group,(C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxy groups,halo(C₁–C₆)alkoxy groups, mono(C₁–C₆)alkylamino groups,di(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent, (C₁–C₆)alkylthio groups, halo(C₁–C₆)alkylthio groups,(C₁–C₆)alkylsulfinyl groups, halo(C₁–C₆)alkylsulfinyl groups,(C₁–C₆)alkylsulfonyl groups, halo(C₁–C₆)alkylsulfonyl groups and(C₁–C₆)alkoxycarbonyl groups; a (C₃–C₆)alkenyl group; ahalo(C₃–C₆)alkenyl group; a (C₃–C₆)alkynyl group; a halo(C₃–C₆)alkynylgroup; a (C₃–C₆)cycloalkyl group; a hydroxyl group; a (C₁–C₆)alkoxygroup; a halo(C₁–C₆)alkoxy group; an amino group; amono(C₁–C₆)alkylamino group; a mono(halo(C₁–C₆)alkyl)amino group; adi(C₁–C₆)alkylamino group whose (C₁–C₆)alkyl groups may be the same ordifferent; a di(halo(C₁–C₆)alkyl)amino group whose halo(C₁–C₆)alkylgroups may be the same or different; a (C₁–C₆)alkylcarbonylamino group;a phenylamino group; a substituted phenylamino group having on the ringone or more substituents which may be the same or different and areselected from halogen atoms, cyano group, nitro group, (C₁–C₆)alkylgroups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxygroups, (C₁–C₆)alkylthio groups, halo(C₁–C₆)alkylthio groups,(C₁–C₆)alkylsulfinyl groups, halo(C₁–C₆)alkylsulfinyl groups,(C₁–C₆)alkylsulfonyl groups, halo(C₁–C₆)alkylsulfonyl groups,mono(C₁–C₆)alkylamino groups, mono(halo(C₁–C₆)alkyl)amino groups,di(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent, di(halo(C₁–C₆)alkyl)amino groups whose halo(C₁–C₆)alkylgroups may be the same or different, (C₁–C₆)alkoxycarbonyl groups and(C₁–C₆)alkylaminocarbonyl groups; a benzoylamino group; a substitutedbenzoylamino group having on the ring one or more substituents which maybe the same or different and are selected from halogen atoms, cyanogroup, nitro group, (C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups,(C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups,halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups,halo(C₁–C₆)alkylsulfonyl groups, mono(C₁–C₆)alkylamino groups,mono(halo(C₁–C₆)alkyl)amino groups, di(C₁–C₆)alkylamino groups whose(C₁–C₆)alkyl groups may be the same or different,di(halo(C₁–C₆)alkyl)amino groups whose halo(C₁–C₆)alkyl groups may bethe same or different, (C₁–C₆)alkoxycarbonyl groups and(C₁–C₆)alkylaminocarbonyl groups; —N═C(T¹)T² (wherein each of T¹ and T²,which may be the same or different, is a hydrogen atom, a (C₁–C₆)alkylgroup, a halo(C₁–C₆)alkyl group, a phenyl group or a substituted phenylgroup having one or more substituents which may be the same or differentand are selected from halogen atoms, cyano group, nitro group,(C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxy groups,halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups, halo(C₁–C₆)alkylthiogroups, (C₁–C₆)alkylsulfinyl groups, halo(C₁–C₆)alkylsulfinyl groups,(C₁–C₆)alkylsulfonyl groups, halo(C₁–C₆)alkylsulfonyl groups,mono(C₁–C₆)alkylamino groups, mono(halo(C₁–C₆)alkyl)amino groups,di(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent, di(halo(C₁–C₆)alkyl)amino groups whose halo(C₁–C₆)alkylgroups may be the same or different, (C₁–C₆)alkoxycarbonyl groups and(C₁–C₆)alkylaminocarbonyl groups); a phenyl group; a substituted phenylgroup having one or more substituents which may be the same or differentand are selected from halogen atoms, cyano group, nitro group,(C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxy groups,halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups, halo(C₁–C₆)alkylthiogroups, (C₁–C₆)alkylsulfinyl groups, halo(C₁–C₆)alkylsulfinyl groups,(C₁–C₆)alkylsulfonyl groups, halo(C₁–C₆)alkylsulfonyl groups,mono(C₁–C₆)alkylamino groups, mono(halo(C₁–C₆)alkyl)amino groups,di(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent, di(halo(C₁–C₆)alkyl)amino groups whose halo(C₁–C₆)alkylgroups may be the same or different, (C₁–C₆)alkoxycarbonyl groups and(C₁–C₆)alkylaminocarbonyl groups; a pyridyl group; or a substitutedpyridyl group having one or more substituents which may be the same ordifferent and are selected from halogen atoms, cyano group, nitro group,(C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxy groups,halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups, halo(C₁–C₆)alkylthiogroups, (C₁–C₆)alkylsulfinyl groups, halo(C₁–C₆)alkylsulfinyl groups,(C₁–C₆)alkylsulfonyl groups, halo(C₁–C₆)alkylsulfonyl groups,mono(C₁–C₆)alkylamino groups, mono(halo(C₁–C₆)alkyl)amino groups,di(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent, di(halo(C₁–C₆)alkyl)amino groups whose halo(C₁–C₆)alkylgroups may be the same or different, and (C₁–C₆)alkoxycarbonyl groups;

each of R², R³ and R⁴, which may be the same or different, is a hydrogenatom, a (C₁–C₆)alkyl group, a (C₃–C₆)alkenyl group, a (C₃–C₆)alkynylgroup, a (C₁–C₄)alkoxy(C₁–C₄)alkyl group or a(C₁–C₄)alkylthio(C₁–C₄)alkyl group, R² being able to bind to A or R¹ toform a 3- to 8-membered ring which may contain one to three atoms thatmay be the same or different and are selected from oxygen atom, sulfuratom and nitrogen atom, and which ring may have one or more substituentsthat may be the same or different and are selected from halogen atoms,(C₁–C₆)alkyl groups and (C₁–C₆)alkoxy groups, and R² being able to betaken together with R¹ to represent ═C(T³)T⁴ (wherein each of T³ and T⁴,which may be the same or different, is a hydrogen atom, a (C₁–C₆)alkylgroup, a halo(C₁–C₆)alkyl group, a (C₁–C₆)alkoxy group, ahalo(C₁–C₆)alkoxy group, an amino group, a mono(C₁–C₆)alkylamino group,a di(C₁–C₆)alkylamino group whose (C₁–C₆)alkyl groups may be the same ordifferent, a mono(halo(C₁–C₆)alkyl)amino group, adi(halo(C₁–C₆)alkyl)amino group whose halo(C₁–C₆)alkyl groups may be thesame or different, a phenyl group or a substituted phenyl group havingone or more substituents which may be the same or different and areselected from halogen atoms, cyano group, nitro group, (C₁–C₆)alkylgroups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxygroups, (C₁–C₆)alkylthio groups, halo(C₁–C₆)alkylthio groups,(C₁–C₆)alkylsulfinyl groups, halo(C₁–C₆)alkylsulfinyl groups,(C₁–C₆)alkylsulfonyl groups, halo(C₁–C₆)alkylsulfonyl groups,mono(C₁–C₆)alkylamino groups, mono(halo(C₁–C₆)alkyl)amino groups,di(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent, di(halo(C₁–C₆)alkyl)amino groups whose halo(C₁–C₆)alkylgroups may be the same or different, (C₁–C₆)alkoxycarbonyl groups and(C₁–C₆)alkylaminocarbonyl groups);

Q is a carbon atom or a nitrogen atom;

each of Xs, which may be the same or different, is a halogen atom, acyano group, a nitro group, an amino group, a (C₁–C₆)alkyl group, ahalo(C₁–C₆)alkyl group, a (C₂–C₆)alkenyl group, a halo(C₂–C₆)alkenylgroup, a (C₂–C₆)alkynyl group, a halo(C₃–C₆)alkynyl group, a(C₁–C₆)alkoxy group, a halo(C₁–C₆)alkoxy group, a(C₁–C₆)alkylcarbonyloxy group, a halo(C₁–C₆)alkylcarbonyloxy group, a(C₁–C₆)alkylthio group, a halo(C₁–C₆)alkylthio group, a(C₁–C₆)alkylsulfinyl group, a halo(C₁–C₆)alkylsulfinyl group, a(C₁–C₆)alkylsulfonyl group, a halo(C₁–C₆)alkylsulfonyl group, a(C₁–C₆)alkylsulfonyloxy group, a halo(C₁–C₆)alkylsulfonyloxy group, amono(C₁–C₆)-alkylamino group, a mono(halo(C₁–C₆)alkyl)amino group, adi(C₁–C₆)alkylamino group whose (C₁–C₆)alkyl groups may be the same ordifferent, a di(halo(C₁–C₆)alkyl)amino group whose halo(C₁–C₆)alkylgroups may be the same or different, a (C₁–C₆)alkylcarbonylamino group,a halo(C₁–C₆)alkylcarbonylamino group, a (C₁–C₆)alkylsulfonylamino groupor a halo(C₁–C₆)alkylsulfonylamino group,

further, two adjacent Xs on the aromatic ring being able to be takentogether to represent a fused ring that may have one or moresubstituents which may be the same or different and are selected fromhalogen atoms, nitro group, cyano group, (C₁–C₆)alkyl groups,halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxy groups, halo(C₁–C₆)alkoxy groups,(C₁–C₆)alkylthio groups, halo(C₁–C₆)alkylthio groups,(C₁–C₆)alkylsulfinyl groups, halo(C₁–C₆)alkylsulfinyl groups,(C₁–C₆)alkylsulfonyl groups, halo(C₁–C₆)alkylsulfonyl groups,mono(C₁–C₆)alkylamino groups, mono(halo(C₁–C₆)alkyl)amino groups,di(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent, and di(halo(C₁–C₆)alkyl)amino groups whose halo(C₁–C₆)alkylgroups may be the same or different, m is an integer of 0 to 2;

each of Ys, which may be the same or different, is a halogen atom; acyano group; a nitro group; a hydroxyl group; a formyl group; a(C₁–C₆)alkyl group; a hydroxy(C₁–C₆)alkyl group; a(C₁–C₆)alkoxy(C₁–C₆)alkyl group; a halo(C₁–C₆)alkoxy(C₁–C₆)alkyl group;a halo(C₁–C₆)alkyl group; a hydroxyhalo(C₁–C₆)alkyl group; a(C₁–C₆)alkoxyhalo(C₁–C₆)alkyl group; a halo(C₁–C₆)alkoxyhalo(C₁–C₆)alkylgroup; a (C₁–C₆)alkoxy group; a halo(C₁–C₆)alkoxy group; ahalo(C₁–C₆)alkoxyhalo(C₁–C₆)alkoxy group; a (C₁–C₆)alkylthio group; ahalo(C₁–C₆)alkylthio group; a (C₁–C₆)alkylsulfinyl group; ahalo(C₁–C₆)alkylsulfinyl group; a (C₁–C₆)alkylsulfonyl group; ahalo(C₁–C₆)alkylsulfonyl group; a halo(C₁–C₆)alkoxyhalo(C₁–C₆)alkylthiogroup; a halo(C₁–C₆)alkoxyhalo(C₁–C₆)alkylsulfinyl group; ahalo(C₁–C₆)alkoxyhalo(C₁–C₆)alkylsulfonyl group; a phenoxy group; asubstituted phenoxy group having one or more substituents which may bethe same or different and are selected from halogen atoms, cyano group,nitro group, (C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxygroups, halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups,halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups andhalo(C₁–C₆)alkylsulfonyl groups; a phenylthio group; a substitutedphenylthio group having one or more substituents which may be the sameor different and are selected from halogen atoms, cyano group, nitrogroup, (C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxygroups, halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups,halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups andhalo(C₁–C₆)alkylsulfonyl groups; a pyridyloxy group; or a substitutedpyridyloxy group having one or more substituents which may be the sameor different and are selected from halogen atoms, cyano group, nitrogroup, (C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxygroups, halo(C₁–C₆)alkoxy groups, (C₁–C₆)alkylthio groups,halo(C₁–C₆)alkylthio groups, (C₁–C₆)alkylsulfinyl groups,halo(C₁–C₆)alkylsulfinyl groups, (C₁–C₆)alkylsulfonyl groups andhalo(C₁–C₆)alkylsulfonyl groups,

further, two adjacent Ys on the aromatic ring being able to be takentogether to represent a fused ring that may have one or moresubstituents which may be the same or different and are selected fromhalogen atoms, nitro group, cyano group, (C₁–C₆)alkyl groups, halo(C₁–C₆)alkyl groups, (C₁–C₆)alkoxy groups, halo (C₁–C₆)alkoxy groups,(C₁–C₆)alkylthio groups, halo(C₁–C₆)alkylthio groups,(C₁–C₆)alkylsulfinyl groups, halo(C₁–C₆)alkylsulfinyl groups,(C₁–C₆)alkylsulfonyl groups, halo(C₁–C₆)alkylsulfonyl groups,mono(C₁–C₆)alkylamino groups, mono(halo(C₁–C₆)alkyl)amino groups,di(C₁–C₆)alkylamino groups whose (C₁–C₆)alkyl groups may be the same ordifferent, and di(halo(C₁–C₆)alkyl)amino groups whose halo(C₁–C₆)alkylgroups may be the same or different, and n is an integer of 0 to 3; anagricultural and horticultural insecticide containing said compound asan active ingredient, and a method of using the same.

MODE FOR CARRYING OUT THE INVENTION

In the definition of general formula (I) for the sulfonamide derivativeof the present invention, the term “halogen atom” means a chlorine atom,a bromine atom, an iodine atom or a fluorine atom. The term“(C₁–C₆)alkyl” means a linear or branched alkyl group of 1 to 6 carbonatoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,s-butyl, t-butyl, n-pentyl, n-hexyl or the like. The term“halo(C₁–C₆)alkyl” means a substituted linear or branched alkyl group of1 to 6 carbon atoms having as the substituent(s) one or more halogenatoms which may be the same or different. The term “(C₃–C₆)cycloalkyl”means a cyclic alkyl group of 3 to 6 carbon atoms, such as cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl or the like. The term“(C₁–C₆)alkylene” means a linear or branched alkylene group of 1 to 6carbon atoms, such as methylene, ethylene, propylene, trimethylene,dimethylmethylene, tetramethylene, isobutylene, dimethylethylene or thelike. The term “(C₂–C₆)alkenylene” means a linear or branched alkenylenegroup of 2 to 6 carbon atoms. The term “(C₂–C₆)alkynylene” means alinear or branched alkynylene group of 2 to 6 carbon atoms.

The “fused ring” includes, for example, naphthalene ring,tetrahydronaphthalene ring, indene ring, indane ring, quinoline ring,quinazoline ring, chroman ring, isochroman ring, indole ring, indolinering, benzodioxane ring, benzodioxole ring, benzofuran ring,dihydrobenzofuran ring, benzothiophene ring, dihydrobenzothiophene ring,benzoxazole ring, benzothiazole ring, benzimidazole ring and indazolering.

The salts of the sulfonamide derivative represented by general formula(I) of the present invention include, for example, inorganic acid saltssuch as hydrochloride, sulfate, nitrate, phosphate and the like; organicacid salts such as acetate, fumarate, maleate, oxalate,methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like; andsalts with a sodium ion, potassium ion, calcium ion or the like.

The sulfonamide derivative of general formula (I) of the presentinvention contains one or more asymmetric carbon atoms or asymmetriccenters in its structural formula in some cases and has two or moreoptical isomers and diastereomers in some cases. The present inventionalso includes all of the individual optical isomers and mixturesconsisting of these isomers in any ratio. The sulfonamide derivative ofgeneral formula (I) of the present invention has two or more geometricalisomers due to one or more carbon-carbon double bonds or carbon-nitrogendouble bonds in its structural formula in some cases. The presentinvention also includes all of the individual geometrical isomers andmixtures consisting of these isomers in any ratio.

In the sulfonamide derivative of general formula (I) of the presentinvention, A is particularly preferably a (C₁–C₆)alkylene group; R¹ ispreferably a hydrogen atom, a (C₁–C₆)alkyl group, a substituted(C₁–C₆)alkyl group, a (C₃–C₆)alkenyl group, a (C₃–C₆)alkynyl group, aphenyl group or a substituted phenyl group, and is particularlypreferably a (C₁–C₆)alkyl group, a (C₁–C₆)alkylthio(C₁–C₆)alkyl group, a(C₁–C₆)alkylsulfinyl(C₁–C₆)alkyl group or a(C₁–C₆)alkylsulfonyl(C₁–C₆)alkyl group; each of R², R₃ and R⁴ ispreferably a hydrogen atom or a (C₁–C₆)alkyl group; Q is preferably acarbon atom or a nitrogen atom, particularly preferably a carbon atom; Xis preferably a halogen atom, a nitro group, a (C₁–C₆)alkyl group, ahalo(C₁–C₆)alkyl group, a halo(C₁–C₆)alkoxy group, a(C₁–C₆)alkylcarbonyloxy group, a (C₁–C₆)alkylsulfonyloxy group or ahalo(C₁–C₆)alkylsulfonyloxy group, and is particularly preferably ahalogen atom; m is preferably 1 or 2, particularly preferably 1; Y ispreferably a halogen atom, a (C₁–C₆)alkyl group, ahalo(C₁–C₆)alkoxy(C₁–C₆)alkyl group, a halo(C₁–C₆)alkyl group, ahydroxyhalo(C₁–C₆)alkyl group, a (C₁–C₆)alkoxyhalo(C₁–C₆)alkyl group, ahalo(C₁–C₆)alkoxyhalo(C₁–C₆)alkyl group, a (C₁–C₆)alkoxy group or a halo(C₁–C₆)alkoxy group, and is particularly preferably a (C₁–C₆)alkyl groupor a halo(C₁–C₆)alkyl group; and n is preferably an integer of 1 to 3,particularly preferably 2.

The sulfonamide derivative of general formula (I) of the presentinvention can be produced, for example, by any of the productionprocesses schematically shown below, but these processes are notintended in any way to limit the scope of the present invention.

Production Processes

wherein A, R¹ to R⁴, X, Y, n, m and Q are as defined above.

The production can be carried out by the above reactions according tothe process disclosed in J. Med. Chem., 10, 982 (1967), JP-A-11-240857,JP-A-2001-131141 or the like. That is, a phthalic anhydride of generalformula (II) is allowed to react with an amine of general formula (III)in the presence of an inert solvent and in the presence or absence of abase or an acid catalyst to obtain a phthalamide of general formula(V-1). When R⁴ is a hydrogen atom in the phthalamide (V-1), thephthalamide (V-1) is converted to an isoimide derivative of generalformula (VI-1) by condensation in the presence of a condensing agent andan inert solvent and in the presence or absence of a base after orwithout isolating the phthalamide (V-1), and the isoimide derivative(VI-1) is allowed to react with a sulfamoylamine of general formula (IV)in the presence of an inert solvent and in the presence or absence of abase or an acid catalyst after or without isolating the isoimidederivative (VI-1), whereby the sulfonamide derivative of general formula(I) can be produced. When R⁴ is a substituent other than a hydrogen atomin the phthalamide (V-1), the sulfonamide derivative of general formula(I) can be produced by condensing the phthalamide (V-1) with asulfamoylamine of general formula (IV) in the presence of a condensingagent and an inert solvent and in the presence or absence of a baseafter or without isolating the phthalamide (V-1).

In addition, a phthalic anhydride of general formula (II) is allowed toreact with a sulfamoylamine of general formula (IV) in the presence ofan inert solvent and in the presence or absence of a base or an acidcatalyst to obtain a phthalamide of general formula (V-2). When R³ is ahydrogen atom in the phthalamide (V-2), the phthalamide (V-2) isconverted to an isoimide derivative of general formula (VI-2) bycondensation in the presence of a condensing agent and an inert solventand in the presence or absence of a base after or without isolating thephthalamide (V-2), and the isoimide derivative (VI-2) is allowed toreact with an amine of general formula (III) in the presence of an inertsolvent and in the presence or absence of a base or an acid catalystafter or without isolating the isoimide derivative (VI-2), whereby thesulfonamide derivative of general formula (I) can be produced. When R³is a substituent other than a hydrogen atom in the phthalamide (V-2),the sulfonamide derivative of general formula (I) can be produced bycondensing the phthalamide (V-2) with an amine of general formula (III)in the presence of a condensing agent and an inert solvent and in thepresence or absence of a base after or without isolating the phthalamide(V-2).

1. General Formula (II)→General Formula (V-1) or General Formula (V-2)

The acid usable in this reaction includes, for example, organic acidssuch as acetic acid, trifluoroacetic acid, etc.; and inorganic acidssuch as hydrochloric acid, sulfuric acid, etc. As to the amount of theacid used, the acid may be used in an amount properly chosen in therange of a catalytic amount to excess moles per mole of the phthalicanhydride of general formula (II). The base includes, for example,organic bases such as triethylamine, pyridine, etc.; and inorganic basessuch as potassium carbonate, sodium hydrogencarbonate, sodium carbonate,sodium hydroxide, etc. As to the amount of the base used, the base maybe used in an amount properly chosen in the range of a catalytic amountto excess moles per mole of the phthalic anhydride of general formula(II).

As the inert solvent used in the reaction, any inert solvent may be usedso long as it does not markedly inhibit the progress of the reaction.There can be exemplified inert solvents including, for example, aromatichydrocarbons such as benzene, toluene, xylene, etc.; halogenatedhydrocarbons such as methylene chloride, chloroform, carbontetrachloride, etc.; halogenated aromatic hydrocarbons such aschlorobenzene, dichlorobenzene, etc.; acyclic or cyclic ethers such asdiethyl ether, dioxane, tetrahydrofuran, etc.; esters such as ethylacetate, etc.; amides such as dimethylformamide, dimethylacetamide,etc,; acids such as acetic acid, etc.; dimethyl sulfoxide; and1,3-dimethyl-2-imidazolidinone. These inert solvents may be used singlyor as a mixture of two or more thereof.

Since the reaction is an equimolar reaction, it is sufficient that thereactants are used in equimolar amounts, though either of them may beused in excess.

As to the reaction temperature, the reaction can be carried out at roomtemperature to the boiling point of the inert solvent used. Although thereaction time is varied depending on the scale of reaction and thereaction temperature, the reaction may be carried out for a periodranging from several minutes to 48 hours.

After completion of the reaction, the desired compound may be used inthe subsequent reaction either after isolation from the reaction systemcontaining the desired compound by a conventional method, or withoutisolation.

The phthalic anhydride of general formula (II) can be produced by theprocess described in J. Org. Chem., 52, 129 (1987), J. Am. Chem. Soc.,51, 1865 (1929), J. Am. Chem. Soc., 63, 1542 (1941) or the like.

2. General Formula (V-1) or General Formula (V-2)→General Formula (I)

As the inert solvent used in this reaction, any inert solvent may beused so long as it does not markedly inhibit the progress of thereaction. There can be exemplified inert solvents including, forexample, halogenated hydrocarbons such as methylene chloride,chloroform, carbon tetrachloride, etc.; acyclic or cyclic ethers such asdiethyl ether, dioxane, tetrahydrofuran, etc.; and nitrites such asacetonitrile, etc. These inert solvents may be used singly or as amixture of two or more thereof.

As the condensing agent used in the reaction, any condensing agent maybe used so long as it is used in conventional amide production. Thecondensing agent includes, for example, trifluoroacetic anhydride,chlorocarbonates, Mukaiyama reagent (2-chloro-N-methylpyridiniumiodide), DCC (1,3-dicyclohexylcarbodiimide), CDI (carbonyl diimidazole)and DEPC (diethyl cyanophosphonate). As to the amount of the condensingagent used, the condensing agent may be used in an amount properlychosen in the range of 1 mole to excess moles per mole of thephthalamide of general formula (V-1) or (V-2).

The base usable in the reaction includes, for example, organic basessuch as triethylamine, pyridine, etc.; and inorganic bases such aspotassium carbonate, etc. As to the amount of the base used, the basemay be used in an amount properly chosen in the range of 1 mole toexcess moles per mole of the phthalamide of general formula (V-1) or(V-2).

As to the reaction temperature, the reaction can be carried out at 0° C.to the boiling point of the inert solvent used. Although the reactiontime is varied depending on the scale of reaction and the reactiontemperature, the reaction may be carried out for a period ranging fromseveral minutes to 48 hours.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by recrystallization, columnchromatography, etc., whereby the desired compound can be produced.

3. General Formula (V-1)→General Formula (VI-1), or General Formula(V-2)→General Formula (VI-2)

In the case of this reaction, the desired compound can be producedaccording to, for example, the process described in J. Med. Chem., 10,982 (1967).

After completion of the reaction, the desired compound may be used inthe subsequent reaction either after isolation from the reaction systemcontaining the desired compound by a conventional method, or withoutisolation.

4. General Formula (VI-1) or General Formula (VI-2)→General Formula (I)

In the case of this reaction, the desired compound can be produced inthe same manner as in the item 1.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by recrystallization, columnchromatography, etc., whereby the desired compound can be produced.

The sulfamoylamine (IV) as starting material can be produced accordingto, for example, any of the processes known in literature andschematically shown below.

wherein R¹, R², R³ and A are as defined above, R⁵ is a protecting groupsuch as a benzyloxycarbonyl group, t-butoxycarbonyl group or alkylsilylgroup, R⁶ is a (C₁–C₆)alkyl group, each of L¹, L² and L³ is a leavinggroup such as a halogen atom, Met is a metal atom such as sodium orpotassium, and Z is a hydrogen atom, a (C₁–C₆)alkyl group or a benzylgroup.(A) General Formula (VII-1)→General Formula (IV)

An amine derivative of general formula (VII-1) is allowed to react witha thiol to obtain a thioalkylamine derivative (VIII-1), according to themethod described in J. Am. Chem. Soc., 58, 1348 (1936), J. Am. Chem.Soc., 60, 1486 (1938) or the like. The thioalkylamine derivative isallowed to react with a halogen after or without isolation of thederivative to obtain a sulfonyl halide derivative of general formula(IX). The sulfonyl halide derivative is allowed to react with an amineof general formula (X) to obtain a sulfonamide derivative of generalformula (IV-1), according to the method described in Synthesis, 1970,545, J. Organic Chem., 21, 667 (1956) or the like. The sulfonamidederivative is subjected to deprotection reaction according to aconventional method, whereby the sulfamoylamine of general formula (IV)can be produced.

(B) General Formula (VII-2)→General Formula (IV)

A disulfide derivative of general formula (VII-2) is converted to asulfenic acid ester derivative (VIII-2) according to the methoddescribed in Synth. Commun., 27, 1321 (1997), Synthesis, 1988, 252 orthe like. The sulfenic acid ester derivative is hydrolyzed after orwithout isolation and the hydrolyzate is allowed to react with a halogenaccording to the method described in J. Am. Chem. Soc., 45, 1068 (1923)or the like to obtain a sulfonyl halide derivative of general formula(IX). Thereafter, the sulfamoylamine of general formula (IV) can beproduced in the same manner as in (A).

(C) General Formula (VII-3)→General Formula (IV)

An amine derivative of general formula (VII-3) is converted to aGrignard reagent (VIII-3) according to the method described in J. Org.Chem., 20, 1159 (1955) or the like, and the Grignard reagent (VIII-3) isallowed to react with sulfuryl chloride to obtain a sulfonyl halidederivative of general formula (IX). Thereafter, the sulfamoylamine ofgeneral formula (IV) can be produced in the same manner as in (A).

(D) General Formula (VII-4)→General Formula (IV)

A sulfenamide derivative of general formula (VIII-4) is obtained from asulfenic acid derivative of general formula (VII-4) and an aminederivative of general formula (X) according to the method described inJ. Am. Chem. Soc., 57, 2172 (1935), Chem. Lett, 1976, 149 or the like.The sulfenamide derivative is converted to a sulfonamide derivative ofgeneral formula (IV-1) according to the method described in J. Org.Chem., 31, 2357 (1966) or the like. Thereafter, the sulfamoylamine ofgeneral formula (IV) can be produced by subjecting the sulfonamidederivative to deprotection in the same manner as in (A).

(E) General Formula (VII-5)→General Formula (IV)

As the sulfamoylamine of general formula (IV), a sulfamoylamine in whicheach of R¹ and R² is a hydrogen atom can be produced by obtaining asulfonamide derivative of general formula (IV-1) from a sulfenatederivative of general formula (VII-5) and hydroxylamine-O-sulfonic acid(XI) according to the method described in Synthesis, 1985, 1032, andthen subjecting the sulfonamide derivative to deprotection in the samemanner as in (A). Such a sulfamoylamine of general formula (IV) can beproduced also by obtaining a sulfonamide derivative of general formula(IV-1) from a sulfenate derivative of general formula (VII-5) and aN-halo-substituted amine of general formula (XII) according to themethod described in J. Org. Chem., 46, 5077 (1981), and then subjectingthe sulfonamide derivative to deprotection in the same manner as in (A).

Typical compounds as the sulfonamide derivative of general formula (I)are listed below in Table 1 and Table 2 but they are not intended in anyway to limit the scope of the present invention. In the followingtables, “n” is a prefix for “normal”, “s” is a prefix for “secondary”,“t” is a prefix for “tertiary”, “i” is a prefix for “iso”, “c” is aprefix for “cyclo”, and “Me” indicates a methyl group, “Et” an ethylgroup, “Pr” a propyl group, “Bu” a butyl group, “Pen” a pentyl group,“Hex” a hexyl group, “Ph” a phenyl group, “Py” a pyridyl group, and “C*”an asymmetric carbon atom. In addition, “J¹”, “J²” and “J³” indicate thefollowing substituents.

TABLE 1 General formula (I-1) (I-1)

Physical property: Melting No. —A—SO₂NR¹R² Xm Yn point ° C. 1-1CHMeCH₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 217–219 1-2 CHMeCH₂SO₂NHMe 3-I2-Me-4-CF(CF₃)₂ 186–188 1-3 CHMeCH₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 122–1251-4 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 170–172 1-5 CHMeCH₂SO₂N(Me)Et 3-I2-Me-4-CF(CF₃)₂ 1-6 CHMeCH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 116 1-7CHMeCH₂SO₂NH-n-Pr 3-I 2-Me-4-CF(CF₃)₂ 147–150 1-8 CHMeCH₂SO₂NH-i-Pr 3-I2-Me-4-CF(CF₃)₂ 204–206 1-9 CHMeCH₂SO₂NH-c-Pr 3-I 2-Me-4-CF(CF₃)₂ 1-10CHMeCH₂SO₂N(n-Pr)₂ 3-I 2-Me-4-CF(CF₃)₂ 1-11 CHMeCH₂SO₂N(i-Pr)₂ 3-I2-Me-4-CF(CF₃)₂ 1-12 CHMeCH₂SO₂NH-n-Bu 3-I 2-Me-4-CF(CF₃)₂ 178–181 1-13CHMeCH₂SO₂NH-s-Bu 3-I 2-Me-4-CF(CF₃)₂ 1-14 CHMeCH₂SO₂NH-t-Bu 3-I2-Me-4-CF(CF₃)₂ 195–197 1-15 CHMeCH₂SO₂NH-i-Bu 3-I 2-Me-4-CF(CF₃)₂ 1-16CHMeCH₂SO₂NH-c-Bu 3-I 2-Me-4-CF(CF₃)₂ 1-17 CHMeCH₂SO₂NH-c-Pen 3-I2-Me-4-CF(CF₃)₂ 1-18 CHMeCH₂SO₂NH-c-Hex 3-I 2-Me-4-CF(CF₃)₂ 1-19CHMeCH₂SO₂NHCH₂-c-Pr 3-I 2-Me-4-CF(CF₃)₂ 1-20 CHMeCH₂SO₂NHCH₂CH═CH₂ 3-I2-Me-4-CF(CF₃)₂ 109–113 1-21 CHMeCH₂SO₂NHCH₂C≡CH 3-I 2-Me-4-CF(CF₃)₂111–113 1-22 CHMeCH₂SO₂NHCH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 200–202 1-23CHMeCH₂SO₂NHCH₂-(2-F—Ph) 3-I 2-Me-4-CF(CF₃)₂ 195–198 1-24CHMeCH₂SO₂NHCH₂-(2-Cl—Ph) 3-I 2-Me-4-CF(CF₃)₂ 193–196 1-25CHMeCH₂SO₂NHCH₂-(2-Br—Ph) 3-I 2-Me-4-CF(CF₃)₂ 189–192 1-26CHMeCH₂SO₂NHCH₂-(2-Me—Ph) 3-I 2-Me-4-CF(CF₃)₂ 1-27CHMeCH₂SO₂NHCH₂-(2-OMe—Ph) 3-I 2-Me-4-CF(CF₃)₂ 180–183 1-28CHMeCH₂SO₂NHCH₂-(2-NO₂—Ph) 3-I 2-Me-4-CF(CF₃)₂ 173–177 1-29CHMeCH₂SO₂NHCH₂-(3-OMe—Ph) 3-I 2-Me-4-CF(CF₃)₂ 196–198 1-30CHMeCH₂SO₂NHCH₂-(3-NO₂—Ph) 3-I 2-Me-4-CF(CF₃)₂ 155–160 1-31CHMeCH₂SO₂NHCH₂-(3-CN—Ph) 3-I 2-Me-4-CF(CF₃)₂ 147–150 1-32CHMeCH₂SO₂NHCH₂-(2,6-(OMe)₂—Ph) 3-I 2-Me-4-CF(CF₃)₂ 210–213 1-33CHMeCH₂SO₂NHCH₂-(4-Cl—Ph) 3-I 2-Me-4-CF(CF₃)₂ 1-34CHMeCH₂SO₂NHCH₂-(4-Me—Ph) 3-I 2-Me-4-CF(CF₃)₂ 1-35CHMeCH₂SO₂NHCH₂-(4-MeO—Ph) 3-I 2-Me-4-CF(CF₃)₂ 176–179 1-36CHMeCH₂SO₂NHCH₂-(4-NO₂—Ph) 3-I 2-Me-4-CF(CF₃)₂ 185–187 1-37CHMeCH₂SO₂NHCH₂-(4-CN—Ph) 3-I 2-Me-4-CF(CF₃)₂ 169–171 1-38CHMeCH₂SO₂NHCH₂-(4-SCF₃—Ph) 3-I 2-Me-4-CF(CF₃)₂ 201–204 1-39CHMeCH₂SO₂NHCH₂-2-Py 3-I 2-Me-4-CF(CF₃)₂ 228–231 1-40CHMeCH₂SO₂NHCH₂-3-Py 3-I 2-Me-4-CF(CF₃)₂ 144–147 1-41CHMeCH₂SO₂NHCH₂-4-Py 3-I 2-Me-4-CF(CF₃)₂ 166–168 1-42CHMeCH₂SO₂N(Me)CH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 186–189 1-43CHMeCH₂SO₂N(Et)CH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 184–186 1-44 CHCH₂SO₂NHCH(Me)Ph3-I 2-Me-4-CF(CF₃)₂ 173–175 1-45 CHMeCH₂SO₂NHC*H(Me)Ph 3-I2-Me-4-CF(CF₃)₂ 168–170 R-enantiomer 1-46 CHMeCH₂SO₂NHC*H(Me)Ph 3-I2-Me-4-CF(CF₃)₂ 159–161 S-enantiomer 1-47 CHMeCH₂SO₂NHCH₂CH₂Ph 3-I2-Me-4-CF(CF₃)₂ 203–206 1-48 CHMeCH₂SO₂NHC(Me)2CH₂Ph 3-I 2-Me-4-CF(CF₃)₂197–198 1-49 CHMeCH₂SO₂N(CH₂)₂ 3-I 2-Me-4-CF(CF₃)₂ 1-50CHMeCH₂SO₂N(CH₂)₃ 3-I 2-Me-4-CF(CF₃)₂ 1-51 CHMeCH₂SO₂N(CH₂)₄ 3-I2-Me-4-CF(CF₃)₂ 1-52 CHMeCH₂SO₂N(CH₂)₅ 3-I 2-Me-4-CF(CF₃)₂ 1-53CHMeCH₂SO₂N(CH₂)₆ 3-I 2-Me-4-CF(CF₃)₂ 1-54 CHMeCH₂SO₂N(CH₂CH₂)₂O 3-I2-Me-4-CF(CF₃)₂ 204–207 1-55 CHMeCH₂SO₂N(CH₂CH₂)₂S 3-I 2-Me-4-CF(CF₃)₂191–194 1-56 CHMeCH₂SO₂N(CH₂CH₂)₂SO 3-I 2-Me-4-CF(CF₃)₂ 195–198 1-57CHMeCH₂SO₂N(CH₂CH₂)₂SO₂ 3-I 2-Me-4-CF(CF₃)₂ 237–240 1-58CMe₂CH₂SO₂N(CH₂CH₂)₂S 3-I 2-Me-4-CF(CF₃)₂ 164–165 1-59CMe₂CH₂SO₂N(CH₂CH₂)₂SO 3-I 2-Me-4-CF(CF₃)₂ 167–168 1-60CMe₂CH₂SO₂N(CH₂CH₂)₂SO₂ 3-I 2-Me-4-CF(CF₃)₂ 166–167 1-61 CMe₂CH₂SO₂J¹3-I 2-Me-4-CF(CF₃)₂ 207–208 1-62 CMe₂CH₂SO₂J² 3-I 2-Me-4-CF(CF₃)₂Amorphous 1-63 CMe₂CH₂SO₂J³ 3-I 2-Me-4-CF(CF₃)₂ 157–159 1-64CHMeCH₂SO₂N(CH₂CH₂)₂NH 3-I 2-Me-4-CF(CF₃)₂ 1-65 CHMeCH₂SO₂N(CH₂CH₂)₂NMe3-I 2-Me-4-CF(CF₃)₂ 1-66 CHMeCH₂SO₂N(CH₂CH₂)₂NOOMe 3-I 2-Me-4-CF(CF₃)₂196–198 1-67 CHMeCH₂SO₂N(CH₂CH₂)₂C═O 3-I 2-Me-4-CF(CF₃)₂ 209–211 1-68CHMeCH₂SO₂NHCH₂CF₃ 3-I 2-Me-4-CF(CF₃)₂ 1-69 CHMeCH₂SO₂NHCH(Me)CF₃ 3-I2-Me-4-CF(CF₃)₂ 1-70 CHMeCH₂SO₂NHCH₂CH═OCl₂ 3-I 2-Me-4-CF(CF₃)₂ 1-71CHMeCH₂SO₂NH(CH₂)₂Cl 3-I 2-Me-4-CF(CF₃)₂ 90–95 1-72 CHMeCH₂SO₂NH(CH₂)₂OH3-I 2-Me-4-CF(CF₃)₂ 171–174 1-73 CHMeCH₂SO₂NH(CH₂)₂OMe 3-I2-Me-4-CF(CF₃)₂ 142–144 1-74 CHMeCH₂SO₂NHCHMeCH₂OMe 3-I 2-Me-4-CF(CF₃)₂1-75 CHMeCH₂SO₂NH(CH₂)₂SMe 3-I 2-Me-4-CF(CF₃)₂ 156–158 1-76CHMeCH₂SO₂NH(CH₂)₂SOMe 3-I 2-Me-4-CF(CF₃)₂ 132–134 1-77CHMeCH₂SO₂NH(CH₂)₂SO₂Me 3-I 2-Me-4-CF(CF₃)₂ 186–189 1-78OMe₂CH₂SO₂NH(CH₂)₂OH 3-I 2-Me-4-CF(CF₃)₂ 150–151 1-79OMe₂CH₂SO₂NH(CH₂)₂OMe 3-I 2-Me-4-CF(CF₃)₂ 167–168 1-80OMe₂CH₂SO₂NH(CH₂)₂OOOMe 3-I 2-Me-4-CF(CF₃)₂ 181–182 1-81OMe₂CH₂SO₂NH(CH₂)₂SMe 3-I 2-Me-4-CF(CF₃)₂ 161–162 1-82OMe₂CH₂SO₂NH(CH₂)₂SOMe 3-I 2-Me-4-CF(CF₃)₂ 154–155 1-83OMe₂CH₂SO₂NH(CH₂)₂SO₂Me 3-I 2-Me-4-CF(CF₃)₂ 151–152 1-84OMe₂CH₂SO₂NH(CH₂)₂SEt 3-I 2-Me-4-CF(CF₃)₂ 166–167 1-85OMe₂CH₂SO₂NH(CH₂)₂SOEt 3-I 2-Me-4-CF(CF₃)₂ 144–145 1-86OMe₂CH₂SO₂NH(CH₂)₂SO₂Et 3-I 2-Me-4-CF(CF₃)₂ 168–169 1-87OMe₂CH₂SO₂NH(CH₂)₂SPh 3-I 2-Me-4-CF(CF₃)₂ 155–156 1-88OMe₂CH₂SO₂NH(CH₂)₂SOPh 3-I 2-Me-4-CF(CF₃)₂ 151–153 1-89OMe₂CH₂SO₂NH(CH₂)₂SO₂Ph 3-I 2-Me-4-CF(CF₃)₂ 170–172 1-90OMe₂CH₂SO₂NH(CH₂)₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-91 CHMeCH₂SO₂NHCHMeCH₂SMe3-I 2-Me-4-CF(CF₃)₂ 190–193 1-92 CHMeCH₂SO₂NHCHMeCH₂SOMe 3-I2-Me-4-CF(CF₃)₂ 130–133 1-93 CHMeCH₂SO₂NHCHMeCH₂SO₂Me 3-I2-Me-4-CF(CF₃)₂ 150–154 1-94 CHMeCH₂SO₂NOMe₂CH₂SMe 3-I 2-Me-4-CF(CF₃)₂157–160 1-95 CHMeCH₂SO₂NH(CH₂)₃OMe 3-I 2-Me-4-CF(CF₃)₂ 1-96OMe₂CH₂SO₂NH(CH₂)₃SMe 3-I 2-Me-4-CF(CF₃)₂ 1-97 OMe₂CH₂SO₂NH(CH₂)₃SOMe3-I 2-Me-4-CF(CF₃)₂ 1-98 OMe₂CH₂SO₂NH(CH₂)₃SO₂Me 3-I 2-Me-4-CF(CF₃)₂1-99 CHMeCH₂SO₂NHCH₂CN 3-I 2-Me-4-CF(CF₃)₂ 1-100 CHMeCH₂SO₂NHCH₂CO₂Me3-I 2-Me-4-CF(CF₃)₂ 1-101 CHMeCH₂SO₂NHCH₂CO₂Et 3-I 2-Me-4-CF(CF₃)₂ 1-102CHMeCH₂SO₂NHCHMeCO₂Me 3-I 2-Me-4-CF(CF₃)₂ 1-103 CHMeCH₂SO₂NHCHMeCONH₂3-I 2-Me-4-CF(CF₃)₂ 228–230 1-104 CHMeCH₂SO₂NHCHMeCONHEt 3-I2-Me-4-CF(CF₃)₂ 176–177 1-105 CHMeCH₂SO₂NHCH₂CONEt₂ 3-I 2-Me-4-CF(CF₃)₂172–174 1-106 CHMeCH₂SO₂NHPh 3-I 2-Me-4-CF(CF₃)₂ 232–234 1-107CHMeCH₂SO₂NH(2-F—Ph) 3-I 2-Me-4-CF(CF₃)₂ 211–212 1-108CHMeCH₂SO₂NH(2-MeO—Ph) 3-I 2-Me-4-CF(CF₃)₂ 101–106 1-109CHMeCH₂SO₂NH(3-F—Ph) 3-I 2-Me-4-CF(CF₃)₂ 235–236 1-110CHMeCH₂SO₂NH(4-F—Ph) 3-I 2-Me-4-CF(CF₃)₂ 228–233 1-111CHMeCH₂SO₂NH(4-MeO—Ph) 3-I 2-Me-4-CF(CF₃)₂ 143–147 1-112CHMeCH₂SO₂NH(4-MeS—Ph) 3-I 2-Me-4-CF(CF₃)₂ 165–170 1-113CHMeCH₂SO₂NH-2-Py 3-I 2-Me-4-CF(CF₃)₂ 1-114 CHMeCH₂SO₂NH-3-Py 3-I2-Me-4-CF(CF₃)₂ 1-115 CHMeCH₂SO₂NHOH 3-I 2-Me-4-CF(CF₃)₂ 1-116CHMeCH₂SO₂NHOMe 3-I 2-Me-4-CF(CF₃)₂ 200–205 1-117 CHMeCH₂SO₂NMeOMe 3-I2-Me-4-CF(CF₃)₂ 1-118 CHMeCH₂SO₂NHNH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-119CHMeCH₂SO₂NMeNH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-120 CHMeCH₂SO₂NMeNHMe 3-I2-Me-4-CF(CF₃)₂ 1-121 CHMeCH₂SO₂NHMe₂ 3-I 2-Me-4-CF(CF₃)₂ 161–166 1-122CHMeCH₂SO₂NHNHPh 3-I 2-Me-4-CF(CF₃)₂ 1-123 CHMeCH₂SO₂NHNHOOMe 3-I2-Me-4-CF(CF₃)₂ 1-124 CHMeCH₂SO₂NHNHOOPh 3-I 2-Me-4-CF(CF₃)₂ 1-125CHMeCH₂SO₂NHN═OMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-126 CHMeCH₂SO₂NHN═CHPh 3-I2-Me-4-CF(CF₃)₂ 1-127 CHMeCH₂SO₂NHN═C(Me)Ph 3-I 2-Me-4-CF(CF₃)₂ 1-128CHMeCH₂SO₂N═CHMe 3-I 2-Me-4-CF(CF₃)₂ 1-129 CHMeCH₂SO₂N═CHEt 3-I2-Me-4-CF(CF₃)₂ 1-130 CHMeCH₂SO₂N═CH-i-Pr 3-I 2-Me-4-CF(CF₃)₂ 1-131CHMeCH₂SO₂N═CHPh 3-I 2-Me-4-CF(CF₃)₂ 1-132 CHMeCH₂SO₂N═CHNHMe 3-I2-Me-4-CF(CF₃)₂ 1-133 CHMeCH₂SO₂N═CHNMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-134CHMeCH₂SO₂N═CHNEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-135 C*HMeCH₂SO₂NH₂ 3-I2-Me-4-CF(CF₃)₂ R-enantiomer 1-136 C*HMeCH₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂S-enantiomer 1-137 C*HMeCH₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ R-enantiomer1-138 C*HMeCH₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-139C*HMeCH₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ R-enantiomer 1-140 C*HMeCH₂SO₂NMe₂3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-141 C*HMeCH₂SO₂NHEt 3-I2-Me-4-CF(CF₃)₂ R-enantiomer 1-142 C*HMeCH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂105–107 S-enantiomer 1-143 C*HMeCH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂R-enantiomer 1-144 C*HMeCH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 159–163S-enantiomer 1-145 C*HMeCH₂SO₂NHCH₂Ph 3-I 2-Me-4-CF(CF₃)₂ R-enantiomer1-146 C*HMeCH₂SO₂NHCH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 158–159 S-enantiomer 1-147C*HMeCH₂SO₂NHC*HMeCH₂SMe 3-I 2-Me-4-CF(CF₃)₂ Amorphous S,S-enantiomer1-148 C*HMeCH₂SO₂NHC*HMeCH₂SOMe 3-I 2-Me-4-CF(CF₃)₂ 115–120S,S-enantiomer 1-149 C*HMeCH₂SO₂NHC*HMeCH₂SO₂Me 3-I 2-Me-4-CF(CF₃)₂Amorphous S,S-enantiomer 1-150 CHMeSO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-151CHMeSO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-152 CHMeSO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂1-153 CHMeSO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-154 CHMeSO₂NEt₂ 3-I2-Me-4-CF(CF₃)₂ 1-155 CHMe(CH₂)₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-156CHMe(CH₂)₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-157 CHMe(CH₂)₂SO₂NMe₂ 3-I2-Me-4-CF(CF₃)₂ 1-158 CHMe(CH₂)₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-159CHMe(CH₂)₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-160 CHMe(CH₂)₂SO₂NH₂ 3-I2-Me-4-CF(CF₃)₂ S-enantiomer 1-161 C*HMe(CH₂)₂SO₂NHMe 3-I2-Me-4-CF(CF₃)₂ S-enantiomer 1-162 C*HMe(CH₂)₂SO₂NMe₂ 3-I2-Me-4-CF(CF₃)₂ S-enantiomer 1-163 C*HMe(CH₂)₂SO₂NHEt 3-I2-Me-4-CF(CF₃)₂ S-enantiomer 1-164 C*HMe(CH₂)₂SO₂NEt₂ 3-I2-Me-4-CF(CF₃)₂ S-enantiomer 1-165 CHMe(CH₂)₃SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂1-166 CHMe(CH₂)₃SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-167 CHMe(CH₂)₃SO₂NMe₂ 3-I2-Me-4-CF(CF₃)₂ 1-168 CHMe(CH₂)₃SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-169CHMe(CH₂)₃SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-170 CHMe(CH₂)₄SO₂NH₂ 3-I2-Me-4-CF(CF₃)₂ 1-171 CHMe(CH₂)₄SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-172CHMe(CH₂)₄SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-173 CHMe(CH₂)₄SO₂NHEt 3-I2-Me-4-CF(CF₃)₂ 1-174 CHMe(CH₂)₄SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-175OMe₂CH₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ Amorphous 1-176 OMe₂CH₂SO₂NHMe 3-I2-Me-4-CF(CF₃)₂ Amorphous 1-177 OMe₂CH₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂151–152 1-178 OMe₂CH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ Amorphous 1-179OMe₂CH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ Amorphous 1-180 OMe₂CH₂SO₂NH-n-Bu 3-I2-Me-4-CF(CF₃)₂ 185–186 1-181 OMe₂CH₂SO₂N(CH₂)₄ 3-I 2-Me-4-CF(CF₃)₂129–130 1-182 OMe₂CH₂SO₂NHCH₂CH═CH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-183OMe₂CH₂SO₂NHCH₂C≡CH 3-I 2-Me-4-CF(CF₃)₂ 1-184 OMe₂CH₂SO₂NHCH₂Ph 3-I2-Me-4-CF(CF₃)₂ 152–153 1-185 OMe₂CH₂SO₂NHPh 3-I 2-Me-4-CF(CF₃)₂ 1-186OMe₂CH₂SO₂NH-2-Py 3-I 2-Me-4-CF(CF₃)₂ 1-187 OMe₂SO₂NH₂ 3-I2-Me-4-CF(CF₃)₂ 1-188 OMe₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-189 OMe₂SO₂NMe₂3-I 2-Me-4-CF(CF₃)₂ 1-190 OMe₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-191OMe₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-192 OMe₂(CH₂)₂SO₂NH₂ 3-I2-Me-4-CF(CF₃)₂ 1-193 OMe₂(CH₂)₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-194OMe₂(CH₂)₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-195 OMe₂(CH₂)₂SO₂NHEt 3-I2-Me-4-CF(CF₃)₂ 1-196 OMe₂(CH₂)₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-197OMe₂(CH₂)₃SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-198 OMe₂(CH₂)₃SO₂NHMe 3-I2-Me-4-CF(CF₃)₂ 1-199 OMe₂(CH₂)₃SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-200OMe₂(CH₂)₃SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 185–186 1-201 OMe₂(CH₂)₃SO₂NEt₂3-I 2-Me-4-CF(CF₃)₂ 142–145 1-202 OMe₂(CH₂)₄SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂1-203 OMe₂(CH₂)₄SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-204 OMe₂(CH₂)₄SO₂NMe₂ 3-I2-Me-4-CF(CF₃)₂ 1-205 OMe₂(CH₂)₄SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-206OMe₂(CH₂)₄SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-207 CHMeCH₂SO₂NHEt H2-Me-4-CF(CF₃)₂ 120–121 1-208 OMe₂CH₂SO₂NEt₂ H 2-Me-4-CF(CF₃)₂ 93–941-209 CHMeCH₂SO₂NHEt 3-F 2-Me-4-CF(CF₃)₂ 1-210 CHMeCH₂SO₂NHEt 3-Cl2-Me-4-CF(CF₃)₂ 1-211 CHMeCH₂SO₂NEt₂ 3-Cl 2-Me-4-CF(CF₃)₂ 103–108 1-212CHMeCH₂SO₂NHEt 3-Br 2-Me-4-CF(CF₃)₂ 136–138 1-213 CHMeCH₂SO₂NMe₂ 3-Br2-Me-4-CF(CF₃)₂ 107–110 1-214 CHMeCH₂SO₂NEt₂ 3-Br 2-Me-4-CF(CF₃)₂112–115 1-215 CHMeCH₂SO₂NH-n-Pr 3-Br 2-Me-4-CF(CF₃)₂ 159–161 1-216CHMeCH₂SO₂NH-i-Pr 3-Br 2-Me-4-CF(CF₃)₂ 185–187 1-217 CHMeCH₂SO₂NH-n-Bu3-Br 2-Me-4-CF(CF₃)₂ 179–181 1-218 CHMeCH₂SO₂NHCH₂Ph 3-Br2-Me-4-CF(CF₃)₂ 139–141 1-219 OMe₂CH₂SO₂NEt₂ 3-Br 2-Me-4-CF(CF₃)₂169–170 1-220 CHMeCH₂SO₂NHEt 3,4-Cl₂ 2-Me-4-CF(CF₃)₂ 1-221CHMeCH₂SO₂NHEt 3,4-Br₂ 2-Me-4-CF(CF₃)₂ 1-222 CHMeCH₂SO₂NHEt 4-Cl2-Me-4-CF(CF₃)₂ 1-223 CHMeCH₂SO₂NHEt 4-Br 2-Me-4-CF(CF₃)₂ 1-224CHMeCH₂SO₂NHEt 4-I 2-Me-4-CF(CF₃)₂ 1-225 CHMeCH₂SO₂NHEt 3-NO₂2-Me-4-CF(CF₃)₂ 1-226 CHMeCH₂SO₂NHEt 3-NH₂ 2-Me-4-CF(CF₃)₂ 1-227CHMeCH₂SO₂NHEt 3-N(CH₃)₂ 2-Me-4-CF(CF₃)₂ 1-228 CHMeCH₂SO₂NHEt 3-NHCOCH₃2-Me-4-CF(CF₃)₂ 1-229 CHMeCH₂SO₂NHEt 3-NHCOCF₃ 2-Me-4-CF(CF₃)₂ 1-230CHMeCH₂SO₂NHEt 3-NHSO₂CH₃ 2-Me-4-CF(CF₃)₂ 1-231 CHMeCH₂SO₂NHEt3-NHSO₂CF₃ 2-Me-4-CF(CF₃)₂ 1-232 CHMeCH₂SO₂NHEt 3-CH₃ 2-Me-4-CF(CF₃)₂1-233 CHMeCH₂SO₂NHEt 3-CF₃ 2-Me-4-CF(CF₃)₂ 1-234 CHMeCH₂SO₂NHEt 3-OCH₃2-Me-4-CF(CF₃)₂ 1-235 CHMeCH₂SO₂NHEt 3-OCF₃ 2-Me-4-CF(CF₃)₂ 1-236CHMeCH₂SO₂NHEt 3-OCOCH₃ 2-Me-4-CF(CF₃)₂ 1-237 CHMeCH₂SO₂NHEt 3-OCOCF₃2-Me-4-CF(CF₃)₂ 1-238 CHMeCH₂SO₂NHEt 3-SCH₃ 2-Me-4-CF(CF₃)₂ 1-239CHMeCH₂SO₂NHEt 3-SOCH₃ 2-Me-4-CF(CF₃)₂ 1-240 CHMeCH₂SO₂NHEt 3-SO₂CH₃2-Me-4-CF(CF₃)₂ 1-241 CHMeCH₂SO₂NHEt 3-SCF₃ 2-Me-4-CF(CF₃)₂ 1-242CHMeCH₂SO₂NHEt 3-SOCF₃ 2-Me-4-CF(CF₃)₂ 1-243 CHMeCH₂SO₂NHEt 3-SO₂CF₃2-Me-4-CF(CF₃)₂ 1-244 CHMeCH₂SO₂NHEt 3-OSO₂CH₃ 2-Me-4-CF(CF₃)₂ 1-245CHMeCH₂SO₂NHEt 3-OSO₂CF₃ 2-Me-4-CF(CF₃)₂ 1-246 CHMeCH₂SO₂NHEt 3-C≡CH2-Me-4-CF(CF₃)₂ 1-247 CHMeCH₂SO₂NHEt 3-C≡CCF₃ 2-Me-4-CF(CF₃)₂ 1-248CHMeCH₂SO₂NHEt 3-CN 2-Me-4-CF(CF₃)₂ 1-249 CHMeCH₂SO₂NHEt 3-CHCHCHCH-42-Me-4-CF(CF₃)₂ 1-250 CHMeCH₂SO₂NHEt 3-OCF₂O-4 2-Me-4-CF(CF₃)₂ 1-251CHMeCH₂SO₂NHEt 3-OCF₂CF₂O-4 2-Me-4-CF(CF₃)₂ 1-252 CHMeCH₂SO₂NHEt 3-I2-Me-4-F 1-253 CHMeCH₂SO₂NHEt 3-I 2-Me-4-Cl 1-254 CHMeCH₂SO₂NHEt 3-I2-Me-4-Br 1-255 CHMeCH₂SO₂NHEt 3-I 2-Me-4-I 1-256 CHMeCH₂SO₂NHEt 3-I2-Me-3-F-4-Cl 1-257 CHMeCH₂SO₂NHEt 3-I 2-Me-3-Cl-4-F 1-258CHMeCH₂SO₂NHEt 3-I 2-Me-3,4-Cl₂ 1-259 CHMeCH₂SO₂NHEt 3-I 2-Me-3-Cl-4-Br1-260 CHMeCH₂SO₂NHEt 3-I 2-Me-3-C1-4-I 1-261 CHMeCH₂SO₂NHEt 3-I 2,4-Cl₂1-262 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-Br 1-263 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-I1-264 CHMeCH₂SO₂NHEt 3-I 2,4-Br₂ 1-265 CHMeCH₂SO₂NHEt 3-I 2-Br-4-I 1-266CHMeCH₂SO₂NHEt 3-I 2,3,4-Cl₃ Amorphous 1-267 CHMeCH₂SO₂NEt₂ 3-I2,3,4-Cl₃ 114–118 1-268 OMe₂CH₂SO₂NEt₂ 3-I 2,3,4-Cl₃ 164–166 1-269CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-F 1-270 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-Br1-271 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-I 1-272 CHMeCH₂SO₂NHEt 3-I2,4-Cl₂-3-Br 1-273 CHMeCH₂SO₂NHEt 3-I 2,4-Cl₂-3-F 1-274 CHMeCH₂SO₂NHEt3-I 2-Me-4-OCHF₂ 1-275 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₃ 181–182 1-276CHMeCH₂SO₂NEt₂ 3-I 2-Me-4-OCF₃ Amorphous 1-277 OMe₂CH₂SO₂NEt₂ 3-I2-Me-4-OCF₃ Amorphous 1-278 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₂CF₃ 1-279CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₂CHF₂ 1-280 CHMeCH₂SO₂NHEt 3-I2-Me-4-OCF₂CHFCF₃ 1-281 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₂CHFOCF₃ 1-282CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₂CHFOC₃F₇-n 1-283 CHMeCH₂SO₂NHEt 3-I2-Cl-4-OCHF₂ 1-284 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF₃ 1-285 CHMeCH₂SO₂NEt₂3-I 2-Cl-4-OCF₃ 100–103 1-286 OMe₂CH₂SO₂NEt₂ 3-I 2-Cl-4-OCF₃ 141–1421-287 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF2CF₃ 1-288 CHMeCH₂SO₂NHEt 3-I2-Cl-4-OCF₂CHF₂ 1-289 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF₂CHFCF₃ 1-290CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF₂CHFOCF₃ 1-291 CHMeCH₂SO₂NHEt 3-I2-Cl-4-OCF₂CHFOC₃F₇-n 1-292 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-OCF₃ 1-293CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-OCF₂CHF₂ 1-294 CHMeCH₂SO₂NHEt 3-I2,3-Cl₂-4-OCF₂CHFCF₃ 1-295 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-OCF₂CHFOCF₃1-296 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-OCF₂CHFOC₃F₇-n 1-297 CHMeCH₂SO₂NHEt3-I 4-CF₂CF₂CF₃ 1-298 CHMeCH₂SO₂NHEt 3-I 4-CF(CF₃)₂ 1-299 CHMeCH₂SO₂NHEt3-I 2-Me-4-CF₃ 1-300 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CF₂CF₃ 1-301CHMeCH₂SO₂NEt₂ 3-I 2-Me-4-CF₂CF₃ 118–120 1-302 OMe₂CH₂SO₂NEt₂ 3-I2-Me-4-CF₂CF₃ Amorphous 1-303 OMe₂CH₂SO₂NHCH₂Ph 3-I 2-Me-4-CF₂CF₃153–154 1-304 OMe₂CH₂SO₂NHCH₂CH₂SMe 3-I 2-Me-4-CF₂CF₃ 164–166 1-305OMe₂CH₂SO₂NHCH₂CH₂SOMe 3-I 2-Me-4-CF₂CF₃ 150–152 1-306OMe₂CH₂SO₂NHCH₂CH₂SO₂Me 3-I 2-Me-4-CF₂CF₃ 139–142 1-307OMe₂CH₂SO₂NHCH₂CH₂SEt 3-I 2-Me-4-CF₂CF₃ 159–160 1-308OMe₂CH₂SO₂NHCH₂CH₂SOEt 3-I 2-Me-4-CF₂CF₃ 198–199 1-309OMe₂CH₂SO₂NHCH₂CH₂SO₂Et 3-I 2-Me-4-CF₂CF₃ 133–134 1-310OMe₂CH₂SO₂NHCH₂CH₂SPh 3-I 2-Me-4-CF₂CF₃ 144–145 1-311 CHMeCH₂SO₂NHEt 3-I2-Me-4-CF₂CF₂CF₃ 1-312 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF₃ 1-313CHMeCH₂SO₂NHEt 3-I 2-F-4-CF₂CF₃ 1-314 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF₂CF₃1-315 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF₂CF₂CF₃ 1-316 CHMeCH₂SO₂NHEt 3-I2-F-4-CF(CF₃)₂ 1-317 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF(CF₃)₂ 1-318CHMeCH₂SO₂NHEt 3-I 2-Br-4-CF(CF₃)₂ 1-319 CHMeCH₂SO₂NHEt 3-I2-I-4-CF(CF₃)₂ 1-320 CHMeCH₂SO₂NHEt 3-I 2-Et-4-CF(CF₃)₂ 1-321CHMeCH₂SO₂NHEt 3-I 2-n-Pr-4-CF(CF₃)₂ 1-322 CHMeCH₂SO₂NHEt 3-I2-i-Pr-4-CF(CF₃)₂ 1-323 CHMeCH₂SO₂NHEt 3-I 2-t-Bu-4-CF(CF₃)₂ 1-324CHMeCH₂SO₂NHEt 3-I 2-Ph-4-CF(CF₃)₂ 1-325 CHMeCH₂SO₂NHEt 3-I2-CH₂OH-4-CF(CF₃)₂ 1-326 CHMeCH₂SO₂NHEt 3-I 2-CH₂OMe-4-CF(CF₃)₂ 1-327CHMeCH₂SO₂NHEt 3-I 2-OMe-4-CF(CF₃)₂ 1-328 CHMeCH₂SO₂NHEt 3-I2-SMe-4-CF(CF₃)₂ 1-329 CHMeCH₂SO₂NHEt 3-I 2-N(Me)₂-4-CF(CF₃)₂ 1-330CHMeCH₂SO₂NHEt 3-I 2-NO₂-4-CF(CF₃)₂ 1-331 CHMeCH₂SO₂NHEt 3-I2-CF₃-4-CF(CF₃)₂ 1-332 CHMeCH₂SO₂NHEt 3-I 2-CHO-4-CF(CF₃)₂ 1-333CHMeCH₂SO₂NHEt 3-I 2-CN-4-CF(CF₃)₂ 1-334 CHMeCH₂SO₂NHEt 3-I2-COMe-4-CF(CF₃)₂ 1-335 CHMeCH₂SO₂NHEt 3-I 2,3-(Me)₂-4-CF(CF₃)₂ 1-336CHMeCH₂SO₂NHEt 3-I 2-Me-3-F-4-CF(CF₃)₂ 1-337 CHMeCH₂SO₂NHEt 3-I2-Me-3-Cl-4-CF(CF₃)₂ 1-338 CHMeCH₂SO₂NHEt 3-I 2-Me-3-OH-4-CF(CF₃)₂ 1-339CHMeCH₂SO₂NHEt 3-I 2-Me-3-OMe-4-CF(CF₃)₂ 1-340 CHMeCH₂SO₂NHEt 3-I2-Me-5-F-4-CF(CF₃)₂ 1-341 CHMeCH₂SO₂NHEt 3-I 2-Me-5-Cl-4-CF(CF₃)₂ 1-342CHMeCH₂SO₂NH₂ 3-I 2-Me-4-CH(CF₃)₂ 214–216 1-343 CHMeCH₂SO₂NHEt 3-I2-Me-4-CH(CF₃)₂ 232–234 1-344 OMe₂CH₂SO₂NEt₂ 3-I 2-Me-4-CH(CF₃)₂Amorphous 1-345 OMe₂CH₂SO₂N(CH₂)₄ 3-I 2-Me-4-CH(CF₃)₂ Amorphous 1-346CHMeCH₂SO₂NHEt 3-I 2-Me-4-C(OH)(CF₃)₂ 1-347 CHMeCH₂SO₂NHEt 3-I2-Me-4-C(OMe)(CF₃)₂ 1-343 CHMeCH₂SO₂NHEt 3-I 2-Me-4-C(OEt)(CF₃)₂ 1-349CHMeCH₂SO₂NHEt 3-I 2-OCF₂O-3-4-CF(CF₃)₂ 1-350 CHMeCH₂SO₂NHEt 3-I2-OCH₂O-3-4-CF(CF₃)₂ 1-351 CHMeCH₂SO₂NHEt 3-I 2-(CH₂)₃-3-4-CF(CF₃)₂1-352 CHMeCH₂SO₂NHEt 3-I 2-(CH₂)₄-3-4-CF(CF₃)₂ 1-353 CHMeCH₂SO₂NHEt 3-I2-Me-4-CF(CF₃)CF₂CF₃

TABLE 2 General formula (I-2) (I-2)

Physical property: Melting No. —A—SO₂NR¹R² Xm Yn point ° C. 2-1CHMeCH₂SO₂NHEt 3-I 4-CF(CF₃)₂ 2-2 CHMeCH₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 2-3CHMeCH₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 2-4 CHMeCH₂SO₂NMe₂ 3-I2-Me-4-CF(CF₃)₂ 2-5 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ Amor- phous 2-6CHMeCH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 2-7 CMe₂CH₂SO₂NEt₂ 3-I2-Me-4-CF(CF₃)₂ Amor- phous 2-8 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF(CF₃)₂ 2-9CHMeCH₂SO₂NHEt 3-I 2-OMe-4-CF(CF₃)₂ 2-10 CHMeCH₂SO₂NHEt 3-I2-SMe-4-CF(CF₃)₂ 2-11 CHMeCH₂SO₂NHEt 3-I 2-SOMe-4-CF(CF₃)₂ 2-12CHMeCH₂SO₂NHEt 3-I 2-SO₂Me-4-CF(CF₃)₂ 2-13 CHMeCH₂SO₂NHEt 3-I2-Et-4-CF(CF₃)₂ 2-14 CHMeCH₂SO₂NHEt 3-I 2-n-Pr-4-CF(CF₃)₂ 2-15CHMeCH₂SO₂NHEt 3-I 4-CH(CF₃)₂ 2-16 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CH(CF₃)₂Amor- phous 2-17 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CH(CF₃)₂ 2-18 CHMeCH₂SO₂NHEt3-I 2-OMe-4-CH(CF₃)₂ 2-19 CHMeCH₂SO₂NHEt 3-I 2-SMe-4-CH(CF₃)₂ 2-20CHMeCH₂SO₂NHEt 3-I 2-SOMe-4-CH(CF₃)₂ 2-21 CHMeCH₂SO₂NHEt 3-I2-SO₂Me-4-CH(CF₃)₂ 2-22 CHMeCH₂SO₂NHEt 3-I 2-Et-4-CH(CF₃)₂ 2-23CHMeCH₂SO₂NHEt 3-I 2-n-Pr-4-CH(CF₃)₂Table 3 shows ¹H-NMR data of compounds having a physical propertyexpressed by the word “amorphous” in Table 1 and Table 2.

TABLE 3 NMR data No. ¹H-NMR[CDCl₃ (or DMSO-d₆)/TMS, δvalues (ppm)] 1-621.30(d, 3H), 1.60(s, 6H), 2.38(s, 3H), 2.80(m, 2H), 3.30(m, (CDCl₃) 3H),3.43(s, 2H), 4.00(m, 1H), 4.50(m, 1H), 6.45(br, 1H), 7.25(m, 1H),7.48(m, 2H), 7.76(d, 1H), 7.98(d, 1H), 8.29(d, 1H), 8.40(br, 1H) 1-1471.09(d, 3H), 1.44(d, 3H), 2.05(s, 3H), 2.37(s, 3H), 2.43(m, (CDCl₃) 2H),3.32(m, 2H), 3.63(m, 1H), 4.63(m, 1H), 5.46(br, 1H), 6.70(br, 1H),7.21(t, 1H), 7.36(d, 1H), 7.44(s, 1H), 7.70(d, 1H), 7.90(m, 2H),8.64(br, 1H) 1-149 1.19(d, 3H), 1.37(d, 3H), 2.33(s, 3H), 2.83(s, 3H),3.52(m, (CDCl₃) 2H), 3.27(d, 2H), 3.98(m, 1H), 4.55(m, 1H), 5.98(br,1H), 6.88(br, 1H), 7.11(t, 1H), 7.33(d, 1H), 7.42(s, 1H), 7.60(m, 1H),7.83(m, 2H), 8.89(br, 1H) 1-175 1.49(s, 6H), 2.35(s, 3H), 3.65(s, 2H),6.91(br, 2H), 7.25(m, (DMSO-d₆) 1H), 7.51(d, 1H), 7.52(s, 1H), 7.70(d,1H), 7.78(d, 1H), 7.99(d, 1H), 8.29(s, 1H), 9.87(br, 1H) 1-176 1.63(s,6H), 2.39(s, 3H), 2.56(d, 3H), 3.41(s, 2H), 4.21(br, (CDCl₃) 1H),6.48(br, 1H), 7.20(m, 1H), 7.47(m, 2H), 7.74(d, 1H), 7.99(d, 1H),8.30(br, 1H), 8.32(d, 1H) 1-178 1.01(t, 3H), 1.61(s, 6H), 2.38(s, 3H),2.98(q, 2H), 3.40(s, (CDCl₃) 2H), 4.52(br, 1H), 6.63(br, 1H), 7.19(m,1H), 7.43(m, 2H), 7.71(d, 1H), 7.95(d, 1H), 8.21(d, 1H), 8.46(br, 1H)1-179 1.08(t, 6H), 1.61(s, 6H), 2.34(s, 3H), 3.12(q, 4H), 3.21(s,(CDCl₃) 2H), 6.75(br, 1H), 7.20(m, 1H), 7.43(m, 2H), 7.75(d, 1H),7.96(d, 1H), 8.37(d, 1H), 8.50(br, 1H) 1-266 1.00(t, 3H), 1.28(d, 3H),2.84(m, 4H), 4.27(m, 1H), (DMSO-d₆) 7.14(br, 1H), 7.28(m, 1H), 7.67(m,3H), 8.03(d, 1H), 8.52(d, 1H), 10.14(br, 1H) 1-276 1.10(t, 6H), 1.46(d,3H), 2.31(s, 3H), 3.15(m, 5H), 3.67(m, (CDCl₃) 1H), 4.60(m, 1H),6.80(br, 1H), 7.04(s, 1H), 7.21(t, 1H), 7.25(d, 1H), 7.74(d, 1H),7.95(d, 1H), 8.01(d, 1H), 8.26(br, 1H) 1-277 1.11(t, 6H), 1.63(s, 6H),2.33(s, 3H), 3.14(q, 4H), 3.20(s, (CDCl₃) 2H), 6.67(br, 1H), 7.12(d,1H), 7.21(m, 2H), 7.77(d, 1H), 7.97(d, 1H), 8.18(d, 1H), 8.30(br, 1H)1-302 1.10(t, 6H), 1.62(s, 6H), 2.38(s, 3H), 3.12(q, 4H), 3.16(s,(CDCl₃) 2H), 6.68(br, 1H), 7.22(m, 1H), 7.43(m, 2H), 7.79(d, 1H),7.99(d, 1H), 8.43(br, 1H), 8.45(d, 1H) 1-344 1.09(t, 6H), 1.62(s, 6H),2.35(s, 3H), 3.13(q, 4H), 3.20(s, (CDCl₃) 2H), 3.99(m, 1H), 6.63(br,1H), 7.26(m, 3H), 7.78(d, 1H), 7.98(d, 1H), 8.33(d, 1H), 8.35(br, 1H)1-345 1.63(s, 6H), 1.78(m, 4H), 2.35(s, 3H), 3.19(m, 4H), 3.26(s,(CDCl₃) 2H), 3.99(m, 1H), 6.68(br, 1H), 7.23(m, 3H), 7.77(d, 1H),7.98(d, 1H), 8.31(d, 1H), 8.33(br, 1H) 2-5 1.05(t, 3H), 1.47(d, 3H),2.59(s, 3H), 3.05(m, 2H), 3.25(d, (CDCl₃) 2H), 4.50(m, 1H), 5.05(br,1H), 6.65(br, 1H), 7.25(m, 1H), 7.45(d, 1H), 7.73(d, 1H), 7.97(d, 1H),8.33(d, 1H), 8.63(br, 1H) 2-7 1.08(t, 6H), 1.63(s, 6H), 2.62(s, 38),3.12(q, 4H), 3.18(s, (CDCl₃) 2H), 6.79(br, 1H), 7.22(m, 1H), 7.53(d,1H), 7.77(d, 1H), 7.98(d, 1H), 8.73(d, 1H), 8.78(br, 1H) 2-16 1.01(t,3H), 1.46(d, 3H), 2.55(s, 3H), 3.03(m, 2H), 3.24(d, (CDCl₃) 2H), 4.40(m,2H), 5.10(br, 1H), 6.65(br, 1H), 7.25(m, 2H), 7.71(d, 1H), 7.93(d, 1H),8.14(d, 1H), 8.74(br, 1H)

EXAMPLES

Typical examples of the present invention are described below but theyshould not be construed as limiting the scope of the invention.

Example 1

Production ofN²-(2-ethylsulfamoyl-1-methylethyl)-3-iodo-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide(compound No. 1–4)

(1-1) In tetrahydrofuran (500 ml) was dissolved 22.53 g (300 mmol) of2-aminopropanol, and then 155.1 g (300 mmol) of a 30% solution ofcarbobenzoxy chloride in toluene and a solution of 36.43 g (360 mmol) oftriethylamine in tetrahydrofuran were slowly dropped thereinto underice-cooling. After the resulting mixture was stirred at room temperaturefor 3 hours, the triethylamine hydrochloride precipitated was filteredunder reduced pressure and washed with ethyl acetate. The filtrate wasconcentrated under reduced pressure and diluted hydrochloric acid wasadded thereto, followed by three runs of extraction with ethyl acetate.The organic layer was washed with saturated aqueous sodiumhydrogencarbonate solution and then saturated aqueous sodium chloridesolution, dried over anhydrous sodium sulfate, and then distilled toremove the solvent, whereby 49.8 g (yield 79%) of benzyl(2-hydroxy-1-methylethyl)carbamate was obtained.

(1-2) In tetrahydrofuran (400 ml) were dissolved 46.5 g (222 mmol) ofbenzyl (2-hydroxy-1-methylethyl)carbamate and 26.96 g (266 mmol) oftriethylamine, and a solution of 27.96 g (244 mmol) of methanesulfonylchloride in tetrahydrofuran was slowly dropped thereinto at 0° C. Afterthe resulting mixture was stirred at room temperature for 5 hours, thetriethylamine hydrochloride precipitated was filtered under reducedpressure and washed with ethyl acetate. The filtrate was concentratedunder reduced pressure and water was added thereto, followed by threeruns of extraction with ethyl acetate. The extract solution was washedwith saturated aqueous sodium hydrogencarbonate solution and thensaturated aqueous sodium chloride solution, and dried over anhydroussodium sulfate. The solvent was distilled off and the crude crystalsthus obtained were washed twice with a solvent (hexane:ethylacetate=4:1) to obtain 49.5 g (yield 78%) of2-(benzyloxycarbonylamino)propyl methanesulfonate.

(1-3) In ethanol (120 ml) was dissolved 34.9 g (120 mmol) of2-(benzyloxycarbonylamino)propyl methanesulfonate, followed by addingdropwise thereto a thiolate separately prepared from 14.42 g (120 mmol)of thioglycolic acid and a solution of sodium ethoxide (120 mmol) inethanol. The reaction was carried out at room temperature for 30 minutesand then at 50° C. for 2 hours, after which the solvent was distilledoff and water was added to the residue, followed by three runs ofextraction with ethyl acetate. The extract solution was washed withsaturated aqueous sodium hydrogencarbonate solution and then saturatedaqueous sodium chloride solution, and dried over anhydrous sodiumsulfate. The solvent was distilled off and the resulting residue waspurified by silica gel column chromatography (hexane:ethyl acetate=4:1)to obtain 34.5 g (yield 92%) of2-(benzyloxycarbonylamino)propylthioacetic acid.

(1-4) In ethyl acetate (150 ml) was dissolved 34.5 g (110 mmol) of2-(benzyloxycarbonylamino)propylthioacetic acid, and a solution (50 ml)of 23.9 g (110 mmol) of m-chloroperbenzoic acid in ethyl acetate wasslowly dropped thereinto at 0° C. After the reaction was carried out atroom temperature for 3 hours, the reaction solution was poured intosaturated aqueous sodium hydrogencarbonate solution, followed byextraction with ethyl acetate. The extract solution was washed threetimes with saturated aqueous sodium hydrogencarbonate solution and thenonce with saturated aqueous sodium chloride solution, and dried overanhydrous sodium sulfate. The solvent was distilled off and the crudecrystals thus obtained were washed twice with a solvent (hexane:ethylacetate=2:1) to obtain 30.38 g (yield 84%) of2-(benzyloxycarbonylamino)propylsulfinylacetic acid.

(1-5) In methanol (300 ml) was suspended 30.38 g (93 mmol) of2-(benzyloxycarbonylamino)propylsulfinylacetic acid, followed by addingthereto 19.04 g (75 mmol) of iodine, and the reaction was carried outwith refluxing for 5 hours. An aqueous sodium hydrogensulfite solutionwas added to the reaction mixture to reduce the excess iodine, afterwhich the solution thus obtained was made weakly basic with saturatedaqueous sodium hydrogencarbonate solution and sodium hydrogencarbonateand the methanol was distilled off. Water was added to the residue,followed by three runs of extraction with ethyl acetate. The extractsolution was washed with saturated aqueous sodium chloride solution anddried over anhydrous sodium sulfate.

The solvent was distilled off and the thus obtained crudebis[2-(benzyloxycarbonylamino)propyl]-disulfide (29 mmol, estimated from¹H-NMR integral ratio) was suspended in ethanol (150 ml), followed byadding thereto 15.66 g (88 mmol) of N-bromosuccinimide in smallportions. The reaction was carried out at room temperature for 3 hours,after which the reaction solution was made weakly basic with saturatedaqueous sodium hydrogencarbonate solution and sodium hydrogencarbonateand the ethanol was distilled off. Water was added to the residue,followed by three runs of extraction with ethyl acetate. The extractsolution was washed three times with water and then once with saturatedaqueous sodium chloride solution and dried over anhydrous sodiumsulfate. The solvent was distilled off and the resulting residue waspurified by silica gel column chromatography (hexane:ethyl acetate=2:1)to obtain 16.0 g (yield 60%) of ethyl2-(benzyloxycarbonylamino)propane-1-sulfinate.

(1-6) In ethanol (7 ml) was dissolved 2.2 g (7.4 mmol) of ethyl2-(benzyloxycarbonylamino)propane-1-sulfinate, and 3.2 g (8 mmol) of 10%aqueous sodium hydroxide solution was slowly dropped thereinto underice-cooling. The reaction was carried out at room temperature for 1hour, after which the ethanol was distilled off and water was added tothe residue, followed by two runs of extraction with methyl t-butylether. The aqueous layer was acidified with concentrated hydrochloricacid, followed by three runs of extraction with ethyl acetate. Theextract solution was washed with saturated aqueous sodium chloridesolution and dried over anhydrous sodium sulfate. The solvent wasdistilled off and the crude crystals thus obtained were washed twicewith a solvent (hexane:ethyl acetate=4:1) to obtain 1.73 g (yield 91%)of 2-(benzyloxycarbonylamino)propane-1-sulfinic acid.

(1-7) In water (10 ml) was dissolved 0.52 g (3.8 mmol) of potassiumcarbonate and 1.73 g (6.7 mmol) of2-(benzyloxycarbonylamino)propane-1-sulfinic acid was added thereto,after which 1.07 g (6.7 mmol) of bromine was added dropwise thereto(water was properly added because crystals were precipitated during thedropwise addition to make stirring difficult). After stirring at roomtemperature for 30 minutes, the crystals were filtered and then washedwith water to obtain 2.30 g (quantitative) of2-(benzyloxycarbonylamino)propane-1-sulfonyl bromide.

(1-8) A solution (5 ml) of 1.44 g (3.3 mmol) of2-(benzyloxycarbonylamino)propane-1-sulfonyl bromide in tetrahydrofuranwas added dropwise to 70% aqueous ethylamine solution (10 ml) underice-cooling. The reaction was carried out at room temperature for 1hour, after which the reaction mixture was poured into dilutedhydrochloric acid, followed by three runs of extraction with ethylacetate. The extract solution was washed with saturated aqueous sodiumchloride solution and dried over anhydrous sodium sulfate. The solventwas distilled off to obtain crudeN-ethyl-2-(benzyloxycarbonylamino)propane-1-sulfonamide, and this crudeproduct was used without further purification in the subsequentreaction.

(1-9) In a bottle for pressure hydrogenation, the inner atmosphere ofwhich had been replaced with argon, was placed 0.07 g of 10% Pd—C, andsuspended by adding ethanol (10 ml) thereto all at once. Then, asolution (20 ml) of the crudeN-ethyl-2-(benzyloxycarbonylamino)propane-1-sulfonamide obtained in(1-8) in ethanol was added thereto and the reaction was carried out for10 hours under pressure (hydrogen pressure: 4 kg/cm²) (during thereaction, the pressure was reduced for reducing the partial pressure ofcarbon monoxide produced, and then was re-increased). The reactionsolution was filtered with Celite and washed with ethanol, and thefiltrate was concentrated under reduced pressure. The crystals thusobtained were washed twice with a solvent (hexane:ethyl acetate=2:1) toobtain 0.27 g {yield from 2-(benzyloxycarbonylamino)propane-1-sulfonylbromide: 50%} of N-ethyl-2-aminopropane-1-sulfonamide.

(1-10) In acetonitrile (100 ml) was dissolved 5.5 g (20 mmol) of3-iodophthalic anhydride, and a solution (20 ml) of 5.5 g (20 mmol) of2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline inacetonitrile was slowly dropped thereinto. After the resulting mixturewas stirred at room temperature for 3 hours, two-thirds of theacetonitrile was distilled off under reduced pressure and the crystalsprecipitated were filtered and then washed with acetonitrile to obtain5.6 g (yield 51%) of6-iodo-N-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamicacid.

(1-11) In methyl t-butyl ether (60 ml) was suspended 5.47 g (10 mmol) of6-iodo-N-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamicacid, and a solution of 3.15 g (15 mmol) of trifluoroacetic anhydride inmethyl t-butyl ether was slowly dropped thereinto. The resulting mixturewas stirred at room temperature for 3 hours and then poured into icewater, followed by three runs of extraction with ethyl acetate. Theextract solution was washed twice with saturated aqueous sodiumhydrogencarbonate solution and then once with saturated aqueous sodiumchloride solution, and dried over anhydrous sodium sulfate. The solventwas distilled off and the crude crystals thus obtained were washed twicewith a solvent (hexane:ethyl acetate=4:1) to obtain 5.0 g (yield 94%) of1,3-dihydro-7-iodo-3-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoro-methyl)ethyl]phenylimino}-2-benzofuran-1-one.

(1-12) In acetonitrile (10 ml) was dissolved 0.42 g (0.8 mmol) of1,3-dihydro-7-iodo-3-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenylimino}-2-benzofuran-1-one,followed by adding thereto 0.13 g (0.8 mmol) of theN-ethyl-2-aminopropane-1-sulfonamide obtained in (1-9), and the reactionwas carried out at room temperature for 10 hours. The solvent wasdistilled off and the crystals precipitated were filtered, and washedwith acetonitrile and then with a mixed solvent (hexane:ethylacetate=4:1) to obtain 0.45 g (yield 81%) ofN²-(2-ethylsulfamoyl-1-methylethyl)-3-iodo-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide.

Melting point: 170–172° C.

Example 2

Production of3-iodo-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-(2-sulfamoyl-1,1-dimethylethyl)phthalamide(compound No. 1–175)

(2-1) In tetrahydrofuran (300 ml) was dissolved 23.86 g (200 mmol) of1,1-dimethyl-2-(methylthio)ethylamine, and 103.4 g (200 mmol) of a 30%solution of carbobenzoxy chloride in toluene and then a solution of24.29 g (240 mmol) of triethylamine in tetrahydrofuran were slowlydropped thereinto under ice-cooling. After the resulting mixture wasstirred at room temperature for 3 hours, the triethylamine hydrochlorideprecipitated was filtered under reduced pressure and washed with ethylacetate. The filtrate was concentrated under reduced pressure and theresidue was purified by silica gel column chromatography (hexane:ethylacetate=4:1) to obtain 36.35 g (yield 72%) of benzyl1,1-dimethyl-2-(methylthio)ethylcarbamate.

(2-2) To a solution of 45.4 g (179 mmol) of benzyl1,1-dimethyl-2-(methylthio)ethylcarbamate in aqueous methanol (obtainedby adding 5.22 g (290 mmol) of water to 150 ml of methanol) was added33.46 g (188 mmol) of N-bromosuccinimide in small portions withstirring. The reaction was carried out at room temperature for 2 hours,after which the reaction solution was made weakly basic with saturatedaqueous sodium hydrogencarbonate solution and then the methanol wasdistilled off. Water was added to the residue, followed by three runs ofextraction with ethyl acetate. The extract solution was washed threetimes with water and then once with saturated aqueous sodium chloridesolution, and dried over anhydrous sodium sulfate. The solvent wasdistilled off and the thus obtained crude benzyl1,1-dimethyl-2-(methylsulfinyl)ethylcarbamate was dissolved in aceticanhydride (150 ml), and the reaction was carried out with refluxing for4 hours. The excess acetic anhydride and acetic acid were distilled offunder reduced pressure to obtain a residue containing crude[2-(benzyloxycarbonylamino)-2-methylpropyl]thiomethyl acetate. Thisresidue was dissolved in methanol (300 ml), followed by adding thereto19.54 g (77 mmol) of iodine, and the reaction was carried out withrefluxing for 5 hours. After the reaction mixture was cooled to roomtemperature, an aqueous sodium hydrogensulfite solution was addedthereto to reduce the excess iodine. The reaction solution was madeweakly basic with saturated aqueous sodium hydrogencarbonate solution,after which the methanol was distilled off. Water was added to theresidue, followed by three runs of extraction with ethyl acetate. Theextract solution was washed with saturated aqueous sodium chloridesolution and dried over anhydrous sodium sulfate. The solvent wasdistilled off and the resulting residue was purified by silica gelcolumn chromatography (hexane:ethyl acetate=4:1) to obtain 10.0 g (yield23%) of bis[2-(benzyloxycarbonylamino)-2-methylpropyl]-disulfide.

(2-3) In ethanol (150 ml) was dissolved 10.0 g (21 mmol) ofbis[2-(benzyloxycarbonylamino)-2-methylpropyl]disulfide, and 11.21 g (63mmol) of N-bromosuccinimide was added thereto in small portions withstirring. The reaction was carried out at room temperature for 2 hours,after which the reaction solution was made weakly basic with saturatedaqueous sodium hydrogencarbonate solution and the ethanol was distilledoff. Water was added to the residue, followed by three runs ofextraction with ethyl acetate. The extract solution was washed threetimes with water and then once with saturated aqueous sodium chloridesolution and dried over anhydrous sodium sulfate. The solvent wasdistilled off and the resulting residue was purified by silica gelcolumn chromatography (hexane:ethyl acetate=2:1) to obtain 10.45 g(yield 83%) of ethyl2-(benzyloxycarbonylamino)-2-methypropane-1-sulfinate.

(2-4) In ethanol (10 ml) was dissolved 0.60 g (2 mmol) of ethyl2-(benzyloxycarbonylamino)-2-methylpropane-1-sulfinate, and 0.9 g (2.2mmol) of 10% aqueous sodium hydroxide solution was slowly droppedthereinto under ice-cooling. The reaction was carried out at roomtemperature for 1 hour and then the ethanol was distilled off. Water (10ml), 0.18 g (2.2 mmol) of sodium acetate and 0.25 g (2.2 mmol) ofhydroxylamine-O-sulfonic acid were added to the residue, and thereaction was carried out at room temperature for 1 hour. The reactionmixture was poured into water, followed by three runs of extraction withethyl acetate. The extract solution was washed with saturated aqueoussodium hydrogencarbonate solution and then saturated aqueous sodiumchloride solution, and dried over anhydrous sodium sulfate. The solventwas distilled off and 0.49 g (yield 86%) of the thus obtained crude2-(benzyloxycarbonylamino)-2-methylpropane-1-sulfonamide was usedwithout further purification in the subsequent reaction.

(2-5) In a bottle for pressure hydrogenation, the inner atmosphere ofwhich had been replaced with argon, was placed 0.20 g of 10% Pd—C, andsuspended by adding acetic acid (5 ml) thereto all at once. Then, asolution (10 ml) of the2-(benzyloxycarbonylamino)-2-methylpropane-1-sulfonamide obtained in(2-4) in acetic acid was added thereto and the reaction was carried outfor 10 hours under pressure (hydrogen pressure: 4 kg/cm²) (during thereaction, the pressure was reduced for reducing the partial pressure ofcarbon monoxide produced, and then was re-increased). The reactionsolution was filtered with Celite and washed with ethanol, after whichthe filtrate was concentrated under reduced pressure and the residue(crude 2-amino-2-methylpropane-1-sulfonamide acetate) was used withoutfurther purification in the subsequent reaction.

(2-6) In acetonitrile (10 ml) was dissolved 0.8 g (1.5 mmol) of1,3-dihydro-7-iodo-3-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenylimino}-2-benzofuran-1-one,followed by adding thereto the crude2-amino-2-methylpropane-1-sulfonamide acetate obtained in (2-5) and 0.17g (1.7 mmol) of triethylamine, and the reaction was carried out at roomtemperature for 30 hours. The solvent was distilled off and theresulting residue was purified by silica gel column chromatography(hexane:ethyl acetate=1:1) to obtain 0.05 g (yield 9%) of3-iodo-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-(2-sulfamoyl-1,1-dimethylethyl)phthalamideas an amorphous substance.

¹H-NMR [DMSO-d₆/TMS, 5 values (ppm)] 1.49(s, 6H), 2.35(s, 3H), 3.65(s,2H), 6.91(br, 2H), 7.25(m, 1H), 7.51(d, 1H), 7.52(s, 1H), 7.70(d, 1H),7.78(d, 1H), 7.99(d, 1H), 8.29(s, 1H), 9.87(br, 1H).

The agrohorticultural insecticides containing the sulfonamide derivativeof general formula (I) or salt thereof of the present invention as anactive ingredient are suitable for controlling various insect pests suchas agrohorticultural insect pests, stored grain insect pests, sanitaryinsect pests, nematodes, etc., which are injurious to paddy rice, fruittrees, vegetables, other crops, flowers, ornamental plants, etc. Theyhave a marked insecticidal effect, for example, on LEPIDOPTERA includingsummer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix(Adoxophyes sp.), Manchurian fruit moth (Grapholita inopinata), orientalfruit moth (Grapholita molesta), soybean pod border (Leguminivoraglycinivorella), mulberry leafroller (Olethreutes mori), tea leafroller(Caloptilia thevivora), Caloptilia sp. (Caloptilia zachrysa), appleleafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrinaastaurota), common white (Piers rapae crucivora), tobacco budworm(Heliothis sp.), codling moth (Laspey resia pomonella), diamondback moth(Plutella xylostella), apple fruit moth (Argyresthia conjugella), peachfruit moth (Carposina niponensis), rice stem borer (Chilo suppressalis),rice leafroller (Cnaphalocrocis medinalis), tobacco moth (Ephestiaelutella), mulberry pyralid (Glyphodes pyloalis), yellow rice borer(Scirpophaga incertulas), rice skipper (Parnara guttata), rice armyworm(Pseudaletia separata), pink borer (Sesamia inferens), common cutworm(Spodoptera litura), beet armyworm (Spodoptera exigua), etc.; HEMIPTERAincluding aster leafhopper (Macrosteles fascifrons), green riceleafhopper (Nephotettix cincticeps), brown rice planthopper (Nilaparvatalugens), whitebacked rice planthopper (Sogatella furcifera), citruspsylla (Diaphorina citri), grape whitefly (Aleurolobus taonabae),sweetpotato whitefly (Bemisia tabaci), greenhouse whitefly (Trialeurodesvaporariorum), turnup aphid (Lipaphis erysimi), green peach aphid (Myzuspersicae), Indian wax scale (Ceroplastes ceriferus), cottony citrusscale (Pulvinaria aurantii), camphor scale (Pseudaonidia duplex), sanJose scale (Comstockaspis perniciosa), arrowhead scale (Unaspisyanonensis), etc.; TYLENCHIDA including soybean beetle (Anomalarufocuprea), Japanese beetle (Popillia japonica), tobacco beetle(Lasioderma serricorne), powderpost beetle (Lyctus brunneus),twenty-eight-spotted ladybird (Epilachna vigintiotopunctata), azuki beanweevil (Callosobruchus chinensis), vegetable weevil (Listroderescostirostris), maize weevil (Sitophilus zeamais), boll weevil(Anthonomus grandis grandis), rice water weevil (Lissorhoptrusoryzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice leafbeetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata),pine shoot beetle (Tomicus piniperda), Colorado potato beetle(Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis),corn rootworm (Diabrotica sp.), etc.; DIPTERA including melon fly(Dacus(Zeugodacus) cucurbitae), oriental fruit fly (Dacus(Bactrocera)dorsalis), rice leafminer (Agromyza oryzae), onion maggot (Deliaantiqua), seedcorn maggot (Delia platura), soybean pod gall midge(Asphondylia sp.), muscid fly (Musca domestica), house mosquito (Culexpipiens pipiens), etc.; TYLENCHIDA including root-lesion nematode(Pratylenchus sp.), coffee root-lesion nematode (Pratylenchus coffeae),potato cyst nematode (Globodera rostochiensis), root-knot nematode(Meloidogyne sp.), citrus nematode (Tylenchulus semipenetrans),Aphelenchus sp. (Aphelenchus avenae), chrysanthemum foliar(Aphelenchoides ritzemabosi), etc.; and ACARINA including citrus redmite (Panonychus citri), European red mite (Panonychus ulmi), carminespider mite (Tetranychus cinnabarinus), Kanzawa spider mite (Tetranychuskanzawai Kishida), two-spotted spider mite (Tetranychus urticae Koch),pink tea rust mite (Acaphylla theae), pink citrus rust mite (Aculopspelekassi), purple tea mite (Calacarus carinatus), pear rust mite(Epitrimerus pyri), etc.

The agrohorticultural insecticide containing the sulfonamide derivativeof general formula (I) or salt thereof of the present invention as anactive ingredient has a marked controlling effect on theabove-exemplified insect pests injurious to paddy field crops, uplandcrops, fruit trees, vegetables, other crops, flowers and ornamentalplants, and the like. Therefore, the desired effect of theagrohorti-cultural insecticide of the present invention can be obtainedby applying the agrohorticultural insecticide to the seeds, paddy fieldwater, stalks and leaves of fruit trees, vegetables, other crops,flowers and ornamental plants, soil, etc., at a season at which theinsect pests are expected to appear, before their appearance or at thetime when their appearance is confirmed.

The agrohorticultural insecticide of the present invention is generallyprepared into conveniently usable forms according to an ordinary mannerfor preparation of agrochemicals.

That is, the sulfonamide derivative of general formula (I) or a saltthereof and, optionally, an adjuvant are blended with a suitable inertcarrier in a proper proportion and prepared into a suitable preparationform such as a suspension, emulsifiable concentrate, solubleconcentrate, wettable powder, granules, dust, tablets, pack or the likethrough dissolution, dispersion, suspension, mixing, impregnation,adsorption or sticking.

The inert carrier usable in the present invention may be either solid orliquid. As a material usable as the solid carrier, there can beexemplified soybean flour, cereal flour, wood flour, bark flour, sawdust, powdered tobacco stalks, powdered walnut shells, bran, powderedcellulose, extraction residues of vegetables, powdered syntheticpolymers or resins, clay (e.g. kaolin, bentonite, and acid clay), talcs(e.g. talc and pyrophyllite), silica powders or flakes {e.g.diatomaceous earth, silica sand, mica and white carbon (synthetic,high-dispersion silicic acid, also called finely divided hydrated silicaor hydrated silicic acid, some of commercially available productscontain calcium silicate as the major component)}, activated carbon,powdered sulfur, pumice, calcined diatomaceous earth, ground brick, flyash, sand, calcium carbonate, calcium phosphate and other inorganic ormineral powders, plastic carriers (e.g. polyethylenes, polypropylenesand poly(vinylidene chloride)s), chemical fertilizers (e.g. ammoniumsulfate, ammonium phosphate, ammonium nitrate, urea and ammoniumchloride), and compost. These materials may be used alone or as amixture of two or more thereof.

A material usable as the liquid carrier is selected from materials thathave solubility in themselves or which are without such solubility butare capable of dispersing a compound as active ingredient with the aidof an adjuvant. The following are typical examples of the liquid carrierand can be used alone or as a mixture of two or more thereof: water;alcohols (e.g. methanol, ethanol, isopropanol, butanol and ethyleneglycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutylketone, diisobutyl ketone and cyclohexanone), ethers (e.g. ethyl ether,dioxane, Cellosolve, dipropyl ether and tetrahydrofuran), aliphatichydrocarbons (e.g. kerosene and mineral oils), aromatic hydrocarbons(e.g. benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes),halogenated hydrocarbons (e.g. dichloroethane, chloroform, carbontetrachloride and chlorobenzene), esters (e.g. ethyl acetate,diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate), amides(e.g. dimethylformamide, diethylformamide and dimethylacetamide),nitriles (e.g. acetonitrile), and dimethyl sulfoxide.

The following are typical examples of the adjuvant, which are useddepending upon purposes and used alone or in combination in some cases,or need not be used at all.

To emulsify, disperse, dissolve and/or wet a compound as activeingredient, a surfactant is used. As the surfactant, there can beexemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylarylethers, polyoxyethylene higher fatty acid esters, polyoxyethyleneresinates, polyoxyethylene sorbitan monolaurate, polyoxyethylenesorbitan monooleate, alkylarylsulfonates, naphthalenesulfonic acidcondensation products, ligninsulfonates and higher alcohol sulfateesters.

Further, to stabilize the dispersion of a compound as active ingredient,tackify it and/or bind it, the adjuvants exemplified below may also beused, namely, there may also be used adjuvants such as casein, gelatin,starch, methyl cellulose, carboxymethyl cellulose, gum arabic,poly(vinyl alcohol)s, turpentine, bran oil, bentonite andligninsulfonates.

To improve the flowability of a solid product, the following adjuvantsmay also be used, namely, there may be used adjuvants such as waxes,stearates, alkyl phosphates, etc.

Adjuvants such as naphthalenesulfonic acid condensation products andpolycondensates of phosphates may be used as a peptizer for dispersibleproducts.

Adjuvants such as silicone oil may also be used as a defoaming agent.

Further, if necessary, functional spreading agents, active enhancerssuch as metabolic decomposition inhibitor like piperonyl butoxide,antifreezing agents such as propylene glycol, antioxidants such as BHT,ultraviolet absorbers, and the like may also be added.

The content of the compound as active ingredient may be varied asrequired, and may be properly chosen in the range of 0.01 to 90 parts byweight per 100 parts by weight of the agrohorticultural insecticide. Forexample, in dusts or granules, the suitable content of the compound asactive ingredient is from 0.01 to 50 parts by weight. In emulsifiableconcentrates or flowable wettable powders, it is also from 0.01 to 50parts by weight.

The agrohorticultural insecticide of the present invention is used tocontrol a variety of insect pests in the following manner: it is appliedto a crop on which the insect pests are expected to appear, or a sitewhere appearance or growth of the insect pests is undesirable, as it isor after being properly diluted with or suspended in water or the like,in an amount effective for control of the insect pests.

The applying dosage of the agrohorticultural insecticide of the presentinvention is varied depending upon various factors such as a purpose,insect pests to be controlled, a growth stage of a plant, tendency ofinsect pests appearance, weather, environmental conditions, apreparation form, an application method, an application site andapplication time. It may be properly chosen in the range of 0.001 g to10 kg, preferably 0.01 g to 1 kg, (in terms of the compound as activeingredient) per 10 areas depending upon purposes.

The agrohorticultural insecticide of the present invention may be usedin admixture with other agrohorticultural insecticides, acaricides,nematocides, fungicides, biotic pesticides or the like in order toexpand both spectrum of controllable insect pest species and the periodof time when effective application is possible or to reduce the dosage.Furthermore, the agrohorticultural insecticide of the present inventionmay be used in admixture with herbicides, plant growth regulators,fertilizers or the like, depending upon application situations.

Typical formulation examples and test examples of the present inventionare described below but they should not be construed as limiting thescope of the invention.

As used in the formulation examples, the terms “part” and “parts” are byweight.

Formulation Example 1

Each compound listed in Table 1 or 2 10 parts Xylene 70 partsN-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl 10parts ether and calcium alkylbenzenesulfonate

An emulsifiable concentrate was prepared by mixing uniformly the aboveingredients to effect dissolution.

Formulation Example 2

Each compound listed in Table 1 or 2  3 parts Clay powder 82 partsDiatomaceous earth powder 15 parts

A dust was prepared by mixing uniformly and grinding the aboveingredients.

Formulation Example 3

Each compound listed in Table 1 or 2 5 parts Mixed powder of bentoniteand clay 90 parts  Calcium ligninsulfonate 5 parts

Granules were prepared by mixing the above ingredients uniformly, andkneading the resulting mixture together with a suitable amount of water,followed by granulation and drying.

Formulation Example 4

Each compound listed in Table 1 or 2 20 parts Mixture of kaolin andsynthetic 75 parts high-dispersion silicic acid Mixture ofpolyoxyethylene nonylphenyl  5 parts ether and calciumalkylbenzenesulfonate

A wettable powder was prepared by mixing uniformly and grinding theabove ingredients.

Test Example 1 Insecticidal Effect on Diamond Back Moth (Plutellaxylostella)

Adult diamond back moths were released and allowed to oviposit on aChinese cabbage seedling. Two days after the release, the seedlinghaving the eggs deposited thereon was immersed for about 30 seconds in aliquid chemical prepared by diluting a preparation containing eachcompound listed in Table 1 or 2 as an active ingredient to adjust theconcentration to 50 ppm. After air-dryness, it was allowed to stand in aroom thermostated at 25° C.

Six days after the immersion, the hatched insects were counted. Themortality was calculated according to the following equation and theinsecticidal effect was judged according to the criterion shown below.The test was carried out with triplicate groups of 10 insects.

${{Corrected}\mspace{14mu}{mortality}\mspace{14mu}(\%)} = {\frac{\begin{matrix}{{Number}\mspace{14mu}{of}} \\{{hatched}\mspace{14mu}{insects}} \\{{in}\mspace{14mu}{untreated}\mspace{14mu}{group}}\end{matrix} - \begin{matrix}{{Number}\mspace{14mu}{of}} \\{{hatched}\mspace{14mu}{insects}} \\{{in}\mspace{14mu}{treated}\mspace{14mu}{group}}\end{matrix}}{\begin{matrix}{{Number}\mspace{14mu}{of}\mspace{14mu}{hatched}\mspace{14mu}{insects}} \\{{in}\mspace{14mu}{untreated}\mspace{14mu}{group}}\end{matrix}} \times 100}$Criterion for Judgment:

A - - - Mortality 100%

B - - - Mortality 99–90%

C - - - Mortality 89–80%

D - - - Mortality 79–50%

E - - - Mortality less than 50%

The result of the above test is shown in Table 4 below.

Test Example 2 Insecticidal Effect on Common Cutworm (Spodoptera litura)

A piece of cabbage leaf (cultivar: Shikidori) was immersed for about 30seconds in a liquid chemical prepared by diluting a preparationcontaining each compound listed in Table 1 or 2 as an active ingredientto adjust the concentration to 50 ppm. After air-dryness, it was placedin a plastic Petri dish with a diameter of 9 cm and inoculated withsecond-instar larvae of common cutworm, after which the dish was closedand then allowed to stand in a room thermostated at 25° C. Eight daysafter the inoculation, the dead and alive were counted. The mortalitywas calculated according to the following equation and the insecticidaleffect was judged according to the criterion shown in Test Example 1.The test was carried out with triplicate groups of 10 insects.

${{Corrected}\mspace{14mu}{mortality}\mspace{14mu}(\%)} = {\frac{\begin{matrix}{{Number}\mspace{14mu}{of}} \\{{alive}\mspace{14mu}{larvae}\mspace{14mu}{in}} \\{{untreated}\mspace{14mu}{group}}\end{matrix} - \begin{matrix}{{Number}\mspace{14mu}{of}} \\{{alive}\mspace{14mu}{larvae}\mspace{14mu}{in}} \\{{treated}\mspace{14mu}{group}}\end{matrix}}{\begin{matrix}{{Number}\mspace{14mu}{of}\mspace{14mu}{alive}\mspace{14mu}{larvae}} \\{{in}\mspace{14mu}{untreated}\mspace{14mu}{group}}\end{matrix}} \times 100}$

The result of the above test is shown in Table 4 below.

Test Example 3 Insecticidal Effect on Smaller Tea Tortrix (Adoxophyessp.)

Tea leaves were immersed for about 30 seconds in a liquid chemicalprepared by diluting a preparation containing each compound listed inTable 1 or 2 as an active ingredient to adjust the concentration to 50ppm. After air-dryness, the tea leaves were placed in a plastic Petridish with a diameter of 9 cm and inoculated with larvae of smaller teatortrix, after which the dish was allowed to stand in a roomthermostated at 25° C. and having a humidity of 70%. Eight days afterthe inoculation, the dead and alive were counted and the insecticidaleffect was judged according to the criterion shown in Test Example 1.The test was carried out with triplicate groups of 10 insects.

The result of the above test is shown in Table 4 below.

TABLE 4 No Test Example 1 Test Example 2 Test Example 3 1-1  A A A 1-2 A A A 1-3  A A A 1-4  A A A 1-6  A A A 1-7  A A A 1-8  A A A 1-12 A A A1-14 A A A 1-20 A A A 1-21 A A A 1-22 A A A 1-23 A A A 1-24 A A A 1-25 AA A 1-27 A A A 1-28 A A A 1-29 A A A 1-30 A A A 1-31 A A A 1-32 A A A1-35 A A A 1-36 A A A 1-37 A A A 1-38 A A A 1-39 A A A 1-40 A A A 1-41 AA A 1-42 A A A 1-43 A A A 1-44 A A A 1-45 A A A 1-46 A A A 1-47 A A A1-48 A C A 1-54 A A A 1-55 A A A 1-56 A A A 1-57 A A A 1-58 A A E 1-59 AA E 1-60 A A E 1-61 A A A 1-62 A A A 1-63 A A A 1-66 A A A 1-67 A E E1-71 A A A 1-72 A A A 1-73 A A A 1-75 A A A 1-76 A A A 1-77 A A A 1-78 AE A 1-79 A A A 1-80 A A A 1-81 A A A 1-82 A A A 1-83 A A A 1-84 A A A1-85 A A A 1-86 A A A 1-87 A A A 1-88 A A A 1-89 A A A 1-91 A A A 1-92 AA A 1-93 A A A 1-94 A A A  1-103 A A A  1-104 A A A  1-105 A A E  1-106A E E  1-107 A C A  1-108 A A A  1-109 A E A  1-110 A E E  1-111 A E E 1-112 A E E  1-116 A D A  1-121 A E E  1-142 A A A  1-144 A A A  1-146A A A  1-147 A A A  1-148 A A A  1-149 A A A  1-175 A A A  1-176 A A A 1-177 A A A  1-178 A A A  1-179 A A A  1-180 A C A  1-181 A A A  1-184A A A  1-200 A A A  1-201 A A A  1-207 A A E  1-208 A E A  1-211 A A A 1-212 A A A  1-213 A A A  1-214 A A A  1-215 A A A  1-216 A A A  1-217A A A  1-218 A A A  1-219 A A A  1-266 A C E  1-267 A C E  1-268 A A A 1-275 A E E  1-276 A E E  1-277 A A A  1-285 A C E  1-286 A A E  1-301A A A  1-302 A A A  1-303 A A A  1-304 A A A  1-305 A A A  1-306 A A A 1-307 A A A  1-308 A A A  1-309 A A A  1-310 A A A  1-342 A A A  1-343A A A  1-344 A A A  1-345 A A A 2-5  A A A 2-7  A A A 2-16 A E A

1. A sulfonamide derivative represented by general formula (I) or a saltthereof:

wherein A is a (C₁–C₆)alkylene group; R¹ is a hydrogen atom; a (C₁–C₆)alkyl group; a substituted (C₁–C₆)alkyl group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, hydroxyl group, (C₁–C₆) alkoxy groups, (C₁–C₆) alkylthiogroups, (C₁–C₆) alkylsulfinyl groups, (C₁–C₆) alkylsulfonyl groups,(C₁–C₆) alkylaminocarbonyl groups, (C₁–C₆) alkylcarbonyloxy groups,phenylthio group, phenyl group, substituted phenyl groups having one ormore substituents which may be the same or different and are selectedfrom halogen atoms, cyano group, nitro group, (C₁–C₆)alkyl groups,(C₁–C₆) alkoxy groups, halo (C₁–C₆) alkylthio groups, and pyridyl group;a (C₃–C₆) alkenyl group; a (C₃–C₆) alkynyl group; a (C₃–C₆)cycloalkylgroup; a hydroxyl group; a (C₁–C₆)alkoxy group; an amino group, aphenylamino group, a substituted phenylamino group having on the ringone or more substituents which may be the same or different and areselected from halogen atoms, (C₁–C₆)alkoxy groups and (C₁–C₆)alkylthiogroups; or a pyridyl group; each of R², R³ and R⁴, which may be the sameor different, is a hydrogen atom, a (C₁–C₆)alkyl group, a (C₃–C₆)alkenyl group, a (C₃–C₆) alkynyl group, a (C₁–C₄) alkoxy(C₁–C₄)alkylgroup or a (C₁–C₄) alkylthio(C₁–C₄ )alkyl group, R² being able to bindto A or R¹ to form a 3- to 8-membered ring which may contain one tothree atoms that may be the same or different and are selected fromoxygen atom, sulfur atom and nitrogen atom, and which ring may have oneor more substituents that may be the same or different and are selectedfrom halogen atoms, (C₁–C₆) alkyl groups and (C₁–C₆) alkoxy groups; Q isa carbon atom or a nitrogen atom; each of Xs, which may be the same ordifferent, is a halogen atom, a nitro group, a (C₁–C₆)alkyl group, ahalo (C₁–C₆) alkyl group, a (C₂–C₆) alkenyl group, a halo (C₂–C₆)alkenyl group, a (C₂–C₆) alkynyl group halo (C₃–C₆) alkynyl group, a(C₁–C₆)alkoxy group, a halo (C₁–C₆) alkoxy group, a(C₁–C₆)alkylcarbonyloxy group, a halo(C₁–C₆)alkylcarbonyloxy group, a(C₁–C₆) alkylthio group, a halo (C₁–C₆) alkylthio group, a (C₁–C₆)aikylsulfinyl group, a halo (C₁–C₆) alkylsulfinyl group, a (C₁–C₆)alkylsulfonyl group, a halo(C₁–C₆)alkylsulfonyl group, a(C₁–C₆)alkylsulfonyloxy group or a haio(C₁–C₆)alkylsulfonyloxy group, mis an integer of 0 to 1: each of Ys, which may be the same or different,is a halogen atom; a (C₁–C₆)alkyl group; a halo (C₁–C₆) alkyl group; ora halo (C₁–C₆) alkoxy group; and n is an integer of 1 to
 3. 2. Anagricultural and horticultural insecticide characterized by containing asulfonamide derivative of general formula (I) or a salt thereofaccording to claim 1 as an active ingredient.
 3. A method for applyingan agricultural and horticultural insecticide, characterized by treatinga crop plant to be protected, soil or a paddy field with an effectiveamount of an agricultural and horticultural insecticide according toclaim 2 in order to protect useful plants against insect pests.